Organocatalysts based on natural and modified amino acids for asymmetric reactions

References

1. Knowles, WS. Asymmetric hydrogenations (nobel lecture). Angew Chem Int Ed 2002;41:1998–2007. https://doi.org/10.1002/1521-3773(20020617)41:12<1998::aid-anie1998>3.0.co;2-8.10.1002/1521-3773(20020617)41:12<1998::AID-ANIE1998>3.0.CO;2-8Suche in Google Scholar

2. Noyori, R. Asymmetric catalysis: science and opportunities (nobel lecture). Angew Chem Int Ed 2002;41:2008–22. https://doi.org/10.1002/1521-3773(20020617)41:12<2008::aid-anie2008>3.0.co;2-4.10.1002/1521-3773(20020617)41:12<2008::AID-ANIE2008>3.0.CO;2-4Suche in Google Scholar

3. Sharpless, KB. Searching for new reactivity (nobel lecture). Angew Chem Int Ed 2002;41:2024–32. https://doi.org/10.1002/1521-3773(20020617)41:12<2024::aid-anie2024>3.0.co;2-o.10.1002/1521-3773(20020617)41:12<2024::AID-ANIE2024>3.0.CO;2-OSuche in Google Scholar

4. Enders, D, Jaeger, K-E. Asymmetric synthesis with chemical and biological methods. NY: Wiley VCH; 2007.10.1002/9783527610648Suche in Google Scholar

5. Berkessel, A, Groger, H, MacMillan, D. Asymmetric organocatalysis: From biomimetic concepts to applications in asymmetric synthesis. NY: Wiley VCH; 2005.10.1002/3527604677Suche in Google Scholar

6. Benjamin, L. Asymmetric organocatalysis. Heidelberg: Springer-Verlag; 2009.Suche in Google Scholar

7. Shaikh, IR. Organocatalysis: key trends in green synthetic chemistry, challenges, scope towards heterogenization, and importance from research and industrial point of view. J Catal 2014;2014:1–35. https://doi.org/10.1155/2014/402860.Suche in Google Scholar

8. Jarvo, ER, Miller, SJ. Amino acid and peptides as asymmetric organocatalysts. Tetrahedron 2002;58:2481–95. https://doi.org/10.1016/s0040-4020(02)00122-9.Suche in Google Scholar

9. Whitesides, GM, Wong, C-H. Enzymes as catalysts in synthetic organic chemistry [new synthetic methods]. Angew Chem Int Ed 1985;24:617–38. https://doi.org/10.1002/anie.198506173.Suche in Google Scholar

10. Schneider, JF, Ladd, CL, Bräse, S. Chapter 5: proline as an asymmetric organocatalyst, in sustainable catalysis: without metals or other endangered elements. London, UK: RSC Publishers; 2015. pp. 79–119. Part 1.10.1039/9781782622093-00079Suche in Google Scholar

11. Agirre, M, Arrieta, A, Arrastia, I, Cossio, FP. Organocatalysts derived from unnatural α-amino acids: scope and applications. Chem Asian J 2019;14:44–66. https://doi.org/10.1002/asia.201801296.Suche in Google Scholar

12. Dalko, P, Moisan, L. In the golden age of organocatalysis. Angew Chem Int Ed 2004;43:5138–75. https://doi.org/10.1002/anie.200400650.Suche in Google Scholar PubMed

13. MacMillan, DWC. The advent and development of organocatalysis. Nature 2008;455:304–8. https://doi.org/10.1038/nature07367.Suche in Google Scholar PubMed

14. Seebach, D. Organic synthesis-where now? Angew Chem Int Ed 1990;29:1320–67. https://doi.org/10.1002/anie.199013201.Suche in Google Scholar

15. Tu, Y, Wang, Z, Shi, Y. An efficient asymmetric epoxidation for trans–olefins mediated by a fructose derived ketone. J Am Chem Soc 1996;118:9806–7. https://doi.org/10.1021/ja962345g.Suche in Google Scholar

16. Denmark, SE, Wu, Z, Crudden, C, Matsuhashi, H. Catalytic epoxidation of alkenes with oxone. 2. Fluoro ketones. J Org Chem 1997;62:8288–9. https://doi.org/10.1021/jo971781y.Suche in Google Scholar PubMed

17. Yang, D, Yip, Y-C, Tang, M-W, Wong, M-K, Zheng, J-H, Cheung, K-K. A C2 symmetric chiral ketone for catalytic asymmetric epoxidation of unfunctionalized olefins. J Am Chem Soc 1996;118:491–2. https://doi.org/10.1021/ja9529549.Suche in Google Scholar

18. Sigman, M, Jacobsen, E. Schiff base catalysts for the asymmetric Strecker reaction identified and optimized from parallel synthetic libraries. J Am Chem Soc 1998;120:4901–2. https://doi.org/10.1021/ja980139y.Suche in Google Scholar

19. Corey, E, Grogan, M. Enantioselective synthesis of α–amino nitriles from N-benzhydryl imines and HCN with a chiral bicyclic guanidine as catalyst. Org Lett 1999;1:157–60. https://doi.org/10.1021/ol990623l.Suche in Google Scholar PubMed

20. Miller, SJ, Copeland, GT, Papaioannou, N, Horstmann, TE, Ruel, EM. Kinetic resolution of alcohols catalyzed by tripeptides containing the N-alkylimidazole substructure. J Am Chem Soc 1998;120:1629–30. https://doi.org/10.1021/ja973892k.Suche in Google Scholar

21. List, B, Lerner, R, Barbas, C. Proline-catalyzed direct asymmetric Aldol reactions. J Am Chem Soc 2000;122:2395–6. https://doi.org/10.1021/ja994280y.Suche in Google Scholar

22. Ahrendt, K, Borths, C, MacMillan, D. New strategies for organic catalysis: the first highly enantioselective organocatalytic Diels–Alder reaction. J Am Chem Soc 2000;122:4243–4. https://doi.org/10.1021/ja000092s.Suche in Google Scholar

23. Wong, CH, Whitesides, W. Enzymes in synthetic organic chemistry. Oxford, UK: Elsevier; 1994.Suche in Google Scholar

24. Johnsson, K, Alleman, RK, Widmer, H, Benner, SA. Synthesis, structure and activity of artificial, rationally designed catalytic polypeptides. Nature 1993;365:530–2. https://doi.org/10.1038/365530a0.Suche in Google Scholar

25. Dalko, P, Moisan, L. Enantioselective organocatalysis. Angew Chem Int Ed 2001;40:3726–48. https://doi.org/10.1002/1521-3773(20011015)40:20<3726::aid-anie3726>3.0.co;2-d.10.1002/9783527610945Suche in Google Scholar

26. Oliveira, VG, Cardoso, MFC, Forezi, LSM. Organocatalysis: a Brief overview on its evolution and applications. Catalysts 2018;8:605–34. https://doi.org/10.3390/catal8120605.Suche in Google Scholar

27. Kotsuki, H, Ikishima, H, Okuyama, A. Organocatalytic asymmetric synthesis using proline and related molecules. Heterocycles 2008;75:493–529. Part 1 and 2 and 2008;75;757–97. https://doi.org/10.3987/rev-07-620.Suche in Google Scholar

28. Venkatraman, J, Shankaramma, SC, Balaram, P. Design of folded peptides. Chem Rev 2001;101:3131–52. https://doi.org/10.1021/cr000053z.Suche in Google Scholar

29. List, B. Proline-catalyzed asymmetric reactions. Tetrahedron 2002;58:5573–90. https://doi.org/10.1016/s0040-4020(02)00516-1.Suche in Google Scholar

30. List, B. Enamine catalysis is a powerful strategy for the catalytic generation and use of carbanion equivalents. Acc Chem Res 2004;37:548–57. https://doi.org/10.1021/ar0300571.Suche in Google Scholar PubMed

31. Vitali, A. Proline-rich peptides: multifunctional bioactive molecules as new potential therapeutic drugs. Curr Protein Pept Sci 2015;16:147–62. https://doi.org/10.2174/1389203716666150102110817.Suche in Google Scholar

32. List, B, Lerner, R, Barbas, C. Proline-catalyzed direct asymmetric Aldol reactions. J Am Chem Soc 2000;122:2395–6. https://doi.org/10.1021/ja994280y.Suche in Google Scholar

33. Eder, U, Sauer, G, Wiechert, R. New type of asymmetric cyclization to optically active steroid CD Partial Structures. Angew Chem Int Ed 1971;10:496–7. https://doi.org/10.1002/anie.197104961.Suche in Google Scholar

34. Hajos, Z, Parrish, D. Asymmetric synthesis of bicyclic intermediates of natural product chemistry. J Org Chem 1974;39:1615–21. https://doi.org/10.1021/jo00925a003.Suche in Google Scholar

35. Sakthivel, K, Notz, W, Bui, T, Barbas, CIII. Amino acid catalyzed direct asymmetric Aldol reactions:  a bioorganic approach to catalytic asymmetric carbon−carbon bond-forming reactions. J Am Chem Soc 2001;123:5260–7. https://doi.org/10.1021/ja010037z.Suche in Google Scholar PubMed

36. Bahmanyar, S, Houk, K. The origin of stereoselectivity in proline-catalyzed intramolecular Aldol reactions. J Am Chem Soc 2001;123:12911–2. https://doi.org/10.1021/ja011714s.Suche in Google Scholar PubMed

37. Bahmanyar, S, Houk, K, Martin, H, List, B. Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular Aldol reactions. J Am Chem Soc 2003;125:2475–9. https://doi.org/10.1021/ja028812d.Suche in Google Scholar PubMed

38. Notz, W, List, B. Catalytic asymmetric synthesis of anti-1,2-diols. J Am Chem Soc 2000;122:7386–7. https://doi.org/10.1021/ja001460v.Suche in Google Scholar

39. Pan, Q, Zou, B, Wang, Y, Ma, D. Diastereoselective Aldol reaction of N,N-dibenzyl-α-amino aldehydes with ketones catalyzed by proline. Org Lett 2004;6:1009–12. https://doi.org/10.1021/ol049927k.Suche in Google Scholar PubMed

40. Casas, J, Sunden, H, Cordova, A. Direct organocatalytic asymmetric α-hydroxymethylation of ketones and aldehydes. Tetrahedron Lett 2004;45:6117–9. https://doi.org/10.1016/j.tetlet.2004.06.062.Suche in Google Scholar

41. Ward, D, Jheengut, V. Proline-catalyzed asymmetric Aldol reactions of tetrahydro-4H-thiopyran-4-one with aldehydes. Tetrahedon Lett 2004;45:8347–50. https://doi.org/10.1016/j.tetlet.2004.09.061.Suche in Google Scholar

42. Pihko, P, Laurikainen, K, Usano, A, Nyberg, A, Kaavi, J. Effect of additives on the proline-catalyzed ketone-aldehyde Aldol reactions. Tetrahedron 2006;62:317–28. https://doi.org/10.1016/j.tet.2005.09.070.Suche in Google Scholar

43. Edin, M, Backvall, E, Cordova, A. Tandem enantioselective organo-and biocatalysis: a direct entry for the synthesis of enantiomerically pure Aldols. Tetrahedron Lett 2004;45:7697–701. https://doi.org/10.1016/j.tetlet.2004.08.079.Suche in Google Scholar

44. Zhou, Y, Shan, Z. Chiral diols: a new class of additives for direct Aldol reaction catalyzed by L-proline. J Org Chem 2006;71:9510–2. https://doi.org/10.1021/jo060802y.Suche in Google Scholar PubMed

45. Sekiguchi, Y, Sasaoka, A, Shimomoto, A, Fujioka, S, Kotsuki, H. High-pressure-promoted asymmetric Aldol reactions of ketones with aldehydes catalyzed by L-proline. Synlett 2003;2003:1655–8.10.1055/s-2003-41424Suche in Google Scholar

46. List, B, Pojarliev, P, Castello, C. Proline-catalyzed asymmetric Aldol reactions between ketones and alpha-unsubstituted aldehydes. Org Lett 2001;3:573–5. https://doi.org/10.1021/ol006976y.Suche in Google Scholar PubMed

47. Bogevig, B, Kumaragurubaran, N, Jorgensen, KA. Direct catalytic asymmetric Aldol reactions of aldehydes. Chem Commun 2002;8:620–1.10.1039/b200681bSuche in Google Scholar PubMed

48. Tokuda, O, Kano, T, Gao, W, Ikemoto, T, Maruoka, K. A Practical synthesis of (S)-2-cyclohexyl-2-phenylglycolic acid via organocatalytic asymmetric construction of a tetrasubstituted carbon center. Org Lett 2005;7:5103–5. https://doi.org/10.1021/ol052164w.Suche in Google Scholar PubMed

49. Shen, Z, Li, B, Wang, L, Zhang, Y. Proline-catalyzed Aldol reactions of acyl cyanides with acetone: an efficient and convenient synthesis of 1, 3-diketones. Tetrahedron Lett 2005;46:8785–8. https://doi.org/10.1016/j.tetlet.2005.10.036.Suche in Google Scholar

50. Funabiki, K, Yamamoto, H, Nagaya, H, Matsui, M. Proline-catalyzed direct asymmetric Aldol reaction of trifluoroacetaldehydeethyl hemiacetal with ketones. Tetrahedron Lett 2006;47:5507–10. https://doi.org/10.1016/j.tetlet.2006.05.165.Suche in Google Scholar

51. Chen, G, Wang, Y, He, H, Gao, S, Yang, X, Hao, X. L-Proline-Catalyzed asymmetric Aldol condensation of N-substituted isatins with acetone. Heterocycles 2006;68:2327–33. https://doi.org/10.3987/com-06-10856.Suche in Google Scholar

52. Blackmond, D, Armstrong, A, Coomber, V, Wells, A. Water in organocatalytic processes: debunking the myths. Angew Chem Int Ed 2007;46:3798–800. https://doi.org/10.1002/anie.200604952.Suche in Google Scholar PubMed

53. Cordova, A, Notz, W. Barbas, C3rd. Direct organocatalytic Aldol reactions in buffered aqueous media. Chem Commun 2002;21:3024–5. https://doi.org/10.1039/b207664k.Suche in Google Scholar

54. Peng, Y, Ding, P, Li, Z, Wang, P, Cheng, P. Proline catalyzed Aldol reactions in aqueous micelles: an environmentally friendly reaction system. Tetrahedron Lett 2003;44:3871–5. https://doi.org/10.1016/s0040-4039(03)00692-0.Suche in Google Scholar

55. Loh, T, Feng, L, Yang, H, Yang, J. L-Proline in an ionic liquid as an efficient and reusable catalyst for direct asymmetric Aldol reactions. Tetrahedron Lett 2002;43:8741–3. https://doi.org/10.1016/s0040-4039(02)02104-4.Suche in Google Scholar

56. Gruttadauria, M, Riela, S, Meo, PL, D’Anna, F, Noto, R. Supported ionic liquid asymmetric catalysis. A new method for chiral catalysts recycling. The case of proline-catalyzed Aldol reaction. Tetrahedron Lett 2004;45:6113–6. https://doi.org/10.1016/j.tetlet.2004.06.066.Suche in Google Scholar

57. Northrup, A, MacMillan, D. The first direct and enantioselective cross-Aldol reaction of aldehydes. J Am Chem Soc 2002;124:6798–9. https://doi.org/10.1021/ja0262378.Suche in Google Scholar

58. Thayumanavan, R, Tanaka, F, Barbas, CIII. Direct organocatalytic asymmetric aldol reactions of α-amino aldehydes:  expedient syntheses of highly enantiomerically enriched anti-β-hydroxy-α-amino acids. Org Lett 2004;6:3541–4. https://doi.org/10.1021/ol0485417.Suche in Google Scholar

59. Kallstrom, S, Erkkila, A, Pihko, P, Sjoholm, R, Sillanpaa, R, Leino, R. Consecutive proline-catalyzed Aldol and Metal-mediated allylation reactions: rapid entries to polypropionates. Synlett 2005;2005:751–6.10.1002/chin.200533032Suche in Google Scholar

60. Pidathala, C, Hoang, L, Vignola, N, List, B. Direct catalytic asymmetric enolexo Aldolizations. Angew Chem Int Ed 2003;42:2785–8. https://doi.org/10.1002/anie.200351266.Suche in Google Scholar

61. Mans, D, Pearson, W. Total synthesis of (+)-Cocaine via desymmetrization of a meso-dialdehyde. Org Lett 2004;6:3305–8. https://doi.org/10.1021/ol048777a.Suche in Google Scholar

62. Bogevig, A, Gothelf, K, Jorgensen, K. Nucleophilic addition of nitrones to ketones: development of a new catalytic asymmetric nitrone-Aldol reaction. Chem Eur J 2002;8:5652–61.10.1002/1521-3765(20021216)8:24<5652::AID-CHEM5652>3.0.CO;2-JSuche in Google Scholar

63. Arno, M, Zaragoza, R, Domingo, L. The nucleophilic addition of nitrones to carbonyl compounds: insights on the nature of the mechanism of the l-proline induced asymmetric reaction from a DFT analysis. Tetrahedron Asymmetry 2004;15:1541–9. https://doi.org/10.1016/j.tetasy.2004.03.031.Suche in Google Scholar

64. Bench, B, Liu, C, Evett, C, Watanabe, C. Proline promoted synthesis of ring-fused homodimers:  self-condensation of α,β-unsaturated aldehydes. J Org Chem 2006;71:9458–63. https://doi.org/10.1021/jo061763t.Suche in Google Scholar

65. List, B, Castello, C. A novel proline-catalyzed three-component reaction of ketones, aldehydes, and Meldrum’s acid. Synlett 2001;2001:1687–9. https://doi.org/10.1055/s-2001-18095.Suche in Google Scholar

66. Ramachary, D, Kishor, M, Reddy, G. Development of drug intermediates by using direct organocatalytic multi-component reactions. Org Biomol Chem 2006;4:1641–445. https://doi.org/10.1039/b602696f.Suche in Google Scholar

67. Chowdari, N, Ramachary, D, Barbas, C. Organocatalytic asymmetric assembly reactions:  one-pot synthesis of functionalized β-amino alcohols from aldehydes, ketones, and azodicarboxylates. Org Lett 2003;5:1685–8. https://doi.org/10.1021/ol034333n.Suche in Google Scholar

68. Kazmaier, U. Amino acids valuable organocatalysts in carbohydrate synthesis. Angew Chem Int Ed 2005;44:2186–8. https://doi.org/10.1002/anie.200462873.Suche in Google Scholar

69. Chowdari, N, Ramachary, D, Cordova, A, Barbas, CIII. Proline-catalyzed asymmetric assembly reactions: enzyme-like assembly of carbohydrates and polyketides from three aldehyde substrates. Tetrahedron Lett 2002;43:9591–5. https://doi.org/10.1016/s0040-4039(02)02412-7.Suche in Google Scholar

70. Casas, J, Engqvist, M, Ibrahem, I, Kaynak, B, Cordova, A. Direct amino acid catalyzed asymmetric synthesis of polyketide sugars. Angew Chem Int Ed 2005;44:1343–5. https://doi.org/10.1002/anie.200461400.Suche in Google Scholar PubMed

71. Northrup, AB, MacMillan, DWC. Two-step synthesis of carbohydrates by selective Aldol reactions. Science 2004;305:1752–5. https://doi.org/10.1126/science.1101710.Suche in Google Scholar PubMed

72. Zhao, G, Liao, W, Cordova, A. Direct one-pot highly enantioselective assembly of polyketide and carbohydrate synthons. Tetrahedron Lett 2006;47:4929–32. https://doi.org/10.1016/j.tetlet.2006.05.018.Suche in Google Scholar

73. Enders, D, Grondal, C. Direct organocatalytic denovo synthesis of carbohydrates. Angew Chem Int Ed 2005;44:1210–2. https://doi.org/10.1002/anie.200462428.Suche in Google Scholar PubMed

74. Suri, J, Ramachary, D, Barbas, CIII. Mimicking dihydroxy acetone phosphate-utilizing aldolases through organocatalysis:  a facile route to carbohydrates and aminosugars. Org Lett 2005;7:1383–5. https://doi.org/10.1021/ol0502533.Suche in Google Scholar PubMed

75. Ibrahem, I, Zou, W, Xu, Y, Córdova, A. Amino acid-catalyzed asymmetric carbohydrate formation: organocatalytic one-step denovo synthesis of keto and amino sugars. Adv Synth Catal 2006;348:211–22. https://doi.org/10.1002/adsc.200505323.Suche in Google Scholar

76. Calderon, F, Doyaguez, E, Fernández-Mayoralas, A. Synthesis of azasugars through a proline-catalyzed reaction. J Org Chem 2006;71:6258–61. https://doi.org/10.1021/jo060568b.Suche in Google Scholar PubMed

77. Sunazuka, T, Handa, M, Nagai, K, Shirahata, T, Harigaya, Y, Otoguro, K, et al.. The first total synthesis of (±)-Arisugacin A, a potent, orally bioavailable inhibitor of acetylcholinesterase. Org Lett 2002;4:367–9. https://doi.org/10.1021/ol017046x.Suche in Google Scholar PubMed

78. Pihko, P, Erkkila, A. Enantioselective synthesis of prelactone-B using a proline-catalyzed crossed-Aldol reaction. Tetrahedron Lett 2003;44:7607–9. https://doi.org/10.1016/j.tetlet.2003.08.060.Suche in Google Scholar

79. Sun, B, Peng, L, Chen, X, Li, Y, Li, Y, Yamasaki, K. Synthesis of (−)-(5R,6S)-6-acetoxyhexadecan-5-olide by l-proline-catalyzed asymmetric Aldol reactions. Tetrahedron Asymmetry 2005;16:1305–7. https://doi.org/10.1016/j.tetasy.2005.02.017.Suche in Google Scholar

80. Ikishima, H, Sekiguchi, Y, Ichikawa, Y, Kotsuki, H. Synthesis of (−)-(5R,6S)-6-acetoxyhexadecanolide based on l-proline-catalyzed asymmetric Aldol reactions. Tetrahedron 2006;62:311–6. https://doi.org/10.1016/j.tet.2005.08.111.Suche in Google Scholar

81. Enders, D, Palecek, J, Grondal, C. A direct organocatalytic entry to sphingoids: asymmetric synthesis of d-arabino- and l-ribo-phytosphingosine. Chem Commun 2006;14:655–7. https://doi.org/10.1039/b515007h.Suche in Google Scholar PubMed

82. Panday, SK. Advances in the chemistry of proline and its derivatives: an excellent amino acid with versatile applications in asymmetric synthesis. Tetrahedron Asymmetry 2011;22:1817–47. https://doi.org/10.1016/j.tetasy.2011.09.013.Suche in Google Scholar

83. Allemann, C, Gordillo, R, Clemente, FR, Cheong, PH-Y, Houk, KN. Theory of asymmetric organocatalysis of Aldol and related Reactions:  rationalizations and predictions. Acc Chem Res 2004;37:558–69. https://doi.org/10.1021/ar0300524.Suche in Google Scholar

84. List, B, Hoang, L, Martin, HJ. New mechanistic studies on the proline-catalyzed Aldol reaction. Proc Natl Acad Sci USA 2004;101:5839–42. https://doi.org/10.1073/pnas.0307979101.Suche in Google Scholar

85. Brown, KL, Damm, L, Dunitz, JD, Eschenmoser, A, Hobi, R, Kratky, C. Structural studies of crystalline enamines. Helv Chim Acta 1978;61:3108–35. https://doi.org/10.1002/hlca.19780610839.Suche in Google Scholar

86. Jung, ME. A review of annulation. Tetrahedron 1976;32:3–31. https://doi.org/10.1016/0040-4020(76)80016-6.Suche in Google Scholar

87. Hoang, L, Bahmanyar, S, Houk, KN, List, B. Kinetic and stereochemical evidence for the involvement of only one proline molecule in the transition states of proline-catalyzed intra- and intermolecular Aldol reactions. J Am Chem Soc 2003;125:16–7. https://doi.org/10.1021/ja028634o.Suche in Google Scholar

88. Rajagopal, D, Moni, MS, Subramanian, S, Swaminathan, S. Proline mediated asymmetric ketol cyclization: a template reaction. Tetrahedron Asymmetry 1999;10:1631–4. https://doi.org/10.1016/s0957-4166(99)00174-3.Suche in Google Scholar

89. Puchot, C, Samuel, O, Dunach, E, Zhao, S, Agami, C, Kagan, HB. Nonlinear effects in asymmetric synthesis. Examples in asymmetric oxidations and aldolization reactions. J Am Chem Soc 1986;108:2353–7. https://doi.org/10.1021/ja00269a036.Suche in Google Scholar PubMed

90. Bahmanyar, S, Houk, KN. Transition states of amine-catalyzed Aldol reactions involving enamine intermediates: theoretical studies of mechanism, reactivity, and stereoselectivity. J Am Chem Soc 2001;123:9922–3. https://doi.org/10.1021/ja011403h.Suche in Google Scholar PubMed

91. Bock, DA, Lehmann, CW, List, B. Crystal structures of proline-derived enamines. Proc Natl Acad Sci USA 2010;107:20636–41. https://doi.org/10.1073/pnas.1006509107.Suche in Google Scholar PubMed PubMed Central

92. Willms, JA, Beel, R, Schmidt, ML, Mundt, C, Engeser, M. A new charge-tagged proline-based organocatalyst for mechanistic studies using electrospray mass spectrometry. Beilstein J Org Chem 2014;10:2027–37. https://doi.org/10.3762/bjoc.10.211.Suche in Google Scholar PubMed PubMed Central

93. Schmid, MB, Zeitler, K, Gschwind, RM. The elusive enamine intermediate in proline-catalyzed Aldol reactions: NMR detection, formation pathway, and stabilization trends. Angew Chem Int Ed 2010;49:4997–5003. https://doi.org/10.1002/anie.200906629.Suche in Google Scholar PubMed

94. Notz, W, Tanaka, F, Barbas, CF. Enamine-based organocatalysis with proline and diamines:  the development of direct catalytic asymmetric Aldol, Mannich, Michael, and Diels−Alder reactions. Acc Chem Res 2004;37:580–91. https://doi.org/10.1021/ar0300468.Suche in Google Scholar PubMed

95. Nielsen, M, Worgull, D, Zweifel, T, Gschwend, B, Bertelsen, S, Jørgensen, KA. Mechanisms in aminocatalysis. Chem Commun 2011;47:632–49. https://doi.org/10.1039/c0cc02417a.Suche in Google Scholar PubMed

96. Yang, H, Wong, MW. (S)-Proline-catalyzed nitro-Michael reactions: towards a better understanding of the catalytic mechanism and enantioselectivity. Org Biomol Chem 2012;10:3229–35. https://doi.org/10.1039/c2ob06993h.Suche in Google Scholar PubMed

97. Betancort, JM, Barbas, CFIII. Catalytic direct asymmetric Michael reactions: taming naked aldehyde donors. Org Lett 2001;3:3737–40. https://doi.org/10.1021/ol0167006.Suche in Google Scholar PubMed

98. List, B, Pojarliev, P, Martin, HJ. Efficient proline-catalyzed Michael additions of unmodified ketones to nitro olefins. Org Lett 2001;3:2423–5. https://doi.org/10.1021/ol015799d.Suche in Google Scholar PubMed

99. Enders, D, Seki, A. Proline-catalyzed enantioselective Michael additions of ketones to nitrostyrene. Synlett 2002;10:26–8. https://doi.org/10.1055/s-2002-19336.Suche in Google Scholar

100. Rasalkar, MS, Potdar, MK, Mohile, SS, Salunkhe, MM. An ionic liquid influenced L-proline catalysed asymmetric Michael addition of ketones to nitrostyrene. J Mol Catal Chem 2005;235:267–70. https://doi.org/10.1016/j.molcata.2005.03.024.Suche in Google Scholar

101. List, B. The direct catalytic asymmetric three-component Mannich reaction. J Am Chem Soc 2000;122:9336–7. https://doi.org/10.1021/ja001923x.Suche in Google Scholar

102. Hayashi, Y, Tsuboi, W, Shoji, M, Suzuki, N. Application of high pressure induced by water-freezing to the direct catalytic asymmetric three-component list−barbas−mannich reaction. J Am Chem Soc 2003;125:11208–9. https://doi.org/10.1021/ja0372513.Suche in Google Scholar PubMed

103. Notz, W, Tanaka, F, Watanabe, S, Chowdari, NS, Turner, JM, Thayumanavan, R, et al.. The direct organocatalytic asymmetric mannich Reaction:  unmodified aldehydes as nucleophiles. J Org Chem 2003;68:9624–34. https://doi.org/10.1021/jo0347359.Suche in Google Scholar PubMed

104. Córdova, A. One-pot organocatalytic direct asymmetric synthesis of γ-amino alcohol derivatives. Synlett 2003;11:1651–4. https://doi.org/10.1055/s-2003-41423.Suche in Google Scholar

105. Yang, JW, Stadler, M, List, B. Proline-catalyzed Mannich reaction of aldehydes with N-Boc-imines. Angew Chem Int Ed 2007;46:609–11. https://doi.org/10.1002/anie.200603188.Suche in Google Scholar PubMed

106. Notz, W, Watanabe, S, Chowdari, NS, Zhong, G, Betancourt, JM, Tanaka, F, et al.. Adv Synth Catal 2004;346:1131–40. https://doi.org/10.1002/adsc.200404114.Suche in Google Scholar

107. Yang, JW, Chandler, C, Stadler, M, Kampen, D, List, B. Proline-catalysed Mannich reactions of acetaldehyde. Nature 2008;452:453–5. https://doi.org/10.1038/nature06740.Suche in Google Scholar PubMed

108. Chandler, C, Galzerano, P, Michrowska, A, List, B. The proline-catalyzed double Mannich reaction of acetaldehyde with N-Boc imines. Angew Chem Int Ed 2009;48:1978–80. https://doi.org/10.1002/anie.200806049.Suche in Google Scholar PubMed

109. Utsumi, N, Zhang, H, Tanaka, F, Barbas, CFIII. A way to highly enantiomerically enriched aza-Morita–Baylis–Hillman–type products. Angew Chem Int Ed 2007;46:1878–80. https://doi.org/10.1002/anie.200603973.Suche in Google Scholar PubMed

110. Vogt, H, Bräse, S. Recent approaches towards the asymmetric synthesis of α,α-disubstituted α-amino acids. Org Biomol Chem 2007;5:406–30. https://doi.org/10.1039/b611091f.Suche in Google Scholar PubMed

111. List, B. Direct catalytic asymmetric α-amination of aldehydes. J Am Chem Soc 2002;124:5656–7. https://doi.org/10.1021/ja0261325.Suche in Google Scholar PubMed

112. Bøgevig, A, Juhl, K, Kumaragurubaran, N, Zhuang, W, Jørgensen, KA. Direct organo-catalytic asymmetric α-amination of aldehydes—a simple approach to optically active α-amino aldehydes, α-amino alcohols, and α-amino acids. Angew Chem Int Ed 2002;41:1790–3.10.1002/chin.200239186Suche in Google Scholar

113. Kumaragurubaran, N, Juhl, K, Zhuang, W, Bøgevig, A, Jørgensen, KA. Direct L-proline-catalyzed asymmetric α-amination of ketones. J Am Chem Soc 2002;124:6254–5. https://doi.org/10.1021/ja026412k.Suche in Google Scholar PubMed

114. Vogt, H, Vanderheiden, S, Bräse, S. Proline-catalysed asymmetric amination of α,α-disubstituted aldehydes: synthesis of configurationally stable enantioenriched α-aminoaldehydes. Chem Commun 2003;7:2448–9. https://doi.org/10.1039/b305465a.Suche in Google Scholar PubMed

115. Nagarkar, AG, Telvekar, VN. L-Proline catalyzed synthesis of various N-substituted urea and unsymmetrical N,N’-disubstituted urea. Lett Org Chem 2018;15:926–30. https://doi.org/10.2174/1570178615666171212145348.Suche in Google Scholar

116. Maleki, A, Firouzi-Haji, R. L-Proline functionalized magnetic nanoparticles: a novel magnetically reusable nanocatalyst for one-pot synthesis of 2,4,6-triarylpyridines. Sci Rep 2018;8:17303. https://doi.org/10.1038/s41598-018-35676-x.Suche in Google Scholar PubMed PubMed Central

117. Kamalraja, J, Sowndarya, R, Perumal, PT. A greener approach for the regioselective synthesis of multifunctionalized indolylpyrrole and indolyltriazolylpyrrole hybrids via Michael addition of α-azido ketones. Synlett 2014;25:2208–12.10.1002/chin.201510139Suche in Google Scholar

118. Zhang, F, Li, C, Qi, C. An efficient and mild synthesis of tetrahydro-4H-indol-4-one derivatives via a domino reaction in water. Synthesis 2013;45:3007–17.10.1002/chin.201414163Suche in Google Scholar

119. Zare, L, Nikpassand, M. Multicomponent synthesis of dihydropyridines catalyzed by l-proline. Chin Chem Lett 2011;22:531–4. https://doi.org/10.1016/j.cclet.2010.12.012.Suche in Google Scholar

120. Kumar, A, Maurya, RA. Synthesis of polyhydroquinoline derivatives through unsymmetric Hantzsch reaction using organocatalysts. Tetrahedron 2007;63:1946–52. https://doi.org/10.1016/j.tet.2006.12.074.Suche in Google Scholar

121. Shi, C-L, Shi, D-Q, Kim, SH, Huang, Z-B, Ji, S-J, Ji, M. A novel and efficient one-pot synthesis of furo[3′,4′:5,6]pyrido[2,3-c]pyrazole derivatives using organocatalysts. Tetrahedron 2008;64:2425–32. https://doi.org/10.1016/j.tet.2007.12.053.Suche in Google Scholar

122. Vachan, BS, Karuppasamy, M, Vinoth, P, Kumar, SV, Perumal, S, Sridharan, V, et al.. Proline and its derivatives as organocatalysts for multicomponent reactions in aqueous media: synergic pathways to the green synthesis of heterocycles. Adv Synth Catal 2020;362:87–110. https://doi.org/10.1002/adsc.201900558.Suche in Google Scholar

123. Behbahani, FK, Alaei, HS. L-proline-catalysed synthesis of functionalized unsymmetrical dihydro-1H-indeno[1,2-b]pyridines. J Chem Sci 2013;125:623–6. https://doi.org/10.1007/s12039-013-0419-5.Suche in Google Scholar

124. Henmi, Y, Makino, K, Yoshitomi, Y, Hara, O, Hamada, Y. Highly efficient synthesis of (R)-and (S)-piperazic acids using proline-catalyzed asymmetric α-hydrazination. Tetrahedron Asymmetry 2000;15:3477–81.10.1016/j.tetasy.2004.09.025Suche in Google Scholar

125. Madhavachary, R, Mallik, R, Ramachary, DB. Organocatalytic enantiospecific total synthesis of butenolides. Molecules 2021:4320. https://doi.org/10.3390/molecules26144320.Suche in Google Scholar PubMed PubMed Central

126. Roy, P, Anjum, SR, Ramachary, DB. One-pot knoevenagel and [4 + 2] cycloaddition as a platform for calliviminones. Org Lett 2020;22:2897–901. https://doi.org/10.1021/acs.orglett.0c00518.Suche in Google Scholar PubMed

127. Pasha, MA, Krishna, AV, Ashok, E, Ramachary, DB. Organocatalytic reductive propargylation: scope and applications. J Org Chem 2019;84:15399–416. https://doi.org/10.1021/acs.joc.9b02415.Suche in Google Scholar PubMed

128. Ramachary, DB, Shruthi, KS. A Brønsted acid-amino acid as a synergistic catalyst for asymmetric list-lerner-barbas aldol reactions. J Org Chem 2016;81:2405–19. https://doi.org/10.1021/acs.joc.5b02896.Suche in Google Scholar PubMed

129. Madhavachary, R, Ramachary, DB. High-Yielding Total synthesis of sexually deceptive chiloglottones and antimicrobial dialkylresorcinols through an organocatalytic reductive coupling reaction. Eur J Org Chem 2014;33:7317–23. https://doi.org/10.1002/ejoc.201403128.Suche in Google Scholar

130. Ramachary, DB, Reddy, YV, Banerjee, A, Banerjee, S. Design, synthesis and biological evaluation of optically pure functionalized spiro [5, 5] undecane-1, 5, 9-triones as HIV-1 inhibitors. Org Biomol Chem 2011;9:7282–6. https://doi.org/10.1039/c1ob06133j.Suche in Google Scholar PubMed

131. Ramachary, DB, Vijayendar Reddy, Y. A general approach to chiral building blocks via direct amino acid-catalyzed cascade three-component reductive alkylations: formal total synthesis of HIV-1 protease inhibitors, antibiotic agglomerins, brefeldin A, and (R)-γ-hexanolide. J Org Chem 2010;75:74–85. https://doi.org/10.1021/jo901799n.Suche in Google Scholar PubMed

132. Ramachary, DB, Kishor, M. Direct catalytic asymmetric synthesis of highly functionalized tetronic acids/tetrahydro-isobenzofuran-1, 5-diones via combination of cascade three-component reductive alkylations and Michael-aldol reactions. Org Biomol Chem 2010;8:2859–67. https://doi.org/10.1039/c003588b.Suche in Google Scholar PubMed

133. Ramachary, DB, Sakthidevi, R. Direct catalytic asymmetric synthesis of highly functionalized 2-methylchroman-2, 4-diols via barbas–list aldol reaction. Chem Eur J 2009;15:4516–22. https://doi.org/10.1002/chem.200900066.Suche in Google Scholar

134. Ramachary, DB, Ramakumar, K, Narayana, VV. Amino acid-catalyzed cascade [3 + 2]-cycloaddition/hydrolysis reactions based on the push–pull dienamine platform: synthesis of highly functionalized NH-1, 2, 3-Triazoles. Chem Eur J 2008;14:9143–7. https://doi.org/10.1002/chem.200801325.Suche in Google Scholar

135. Ramachary, DB, Kishor, M. Direct amino acid-catalyzed cascade biomimetic reductive alkylations: application to the asymmetric synthesis of Hajos–Parrish ketone analogues. Org Biomol Chem 2008;6:4176–87. https://doi.org/10.1039/b807999d.Suche in Google Scholar

136. Ramachary, DB, Kishor, M. Organocatalytic sequential one-pot double cascade asymmetric synthesis of Wieland− Miescher ketone analogues from a knoevenagel/hydrogenation/robinson annulation sequence: scope and applications of organocatalytic biomimetic reductions. J Org Chem 2007;72:5056–68. https://doi.org/10.1021/jo070277i.Suche in Google Scholar

137. Ramachary, DB, Chowdari, NS, Barbas, CFIII. Organocatalytic asymmetric domino knoevenagel/diels–alder reactions: a bioorganic approach to the diastereospecific and enantioselective construction of highly substituted spiro [5, 5] undecane-1, 5, 9-triones. Angew Chem 2003;42:4233–7. https://doi.org/10.1002/anie.200351916.Suche in Google Scholar

138. Ramachary, DB, Barbas, CF. Direct amino acid-catalyzed asymmetric desymmetrization of meso-compounds: tandem aminoxylation/O− N bond heterolysis reactions. Org Lett 2005;7:1577–80. https://doi.org/10.1021/ol050246e.Suche in Google Scholar

139. Danishefsky, S, Cain, P. Pyridine route to optically active estrone and 19-norsteroids. J Am Chem Soc 1975;97:5282–4. https://doi.org/10.1021/ja00851a046.Suche in Google Scholar

140. Corey, EJ, Virgil, SC. Enantioselective total synthesis of a protosterol, 3β, 20- dihydroxyprotost-24-ene. J Am Chem Soc 1990;112:6429–31. https://doi.org/10.1021/ja00173a059.Suche in Google Scholar

141. Shimizu, I, Naito, Y, Tsuji, J. Synthesis of optically active (+)-19-nortestosterone by asymmetric bis-annulation reaction. Tetrahedron Lett 1980;21:487–90. https://doi.org/10.1016/s0040-4039(00)71440-7.Suche in Google Scholar

142. Xu, L-W, Lu, Y. Primary amino acids: privileged catalysts in enantioselective organocatalysis. Org & Bio Chem 2008;6:2021–16.10.1039/b803116aSuche in Google Scholar PubMed

143. Amedjkouh, M. Primary amine catalyzed direct asymmetric aldol reaction assisted by water. Tetrahedron Asymmetry 2005;16:1411–4. https://doi.org/10.1016/j.tetasy.2005.02.031.Suche in Google Scholar

144. Tanaka, F, Thayumanavan, R, Mase, N, Barbas, CFIII. Rapid analysis of solvent effects on enamine formation by fluorescence: how might enzymes facilitate enamine chemistry with primary amines? Tetrahedron Lett 2004;45:325–8. https://doi.org/10.1016/j.tetlet.2003.10.157.Suche in Google Scholar

145. C´ordova, A, Zou, W, Ibrahem, I, Reyes, E, Engqvist, M, Liao, WW. Acyclic amino acid-catalyzed direct asymmetric aldol reactions: alanine, the simplest stereoselective organocatalyst. Chem Commun 2005;36:3586–8. https://doi.org/10.1039/b507968n.Suche in Google Scholar PubMed

146. C´ordova, A, Zou, W, Dziedzic, P, Ibrahem, I, Reyes, E, Xu, Y. Direct asymmetric intermolecular aldol reactions catalyzed by amino acids and small peptides. Chem Eur J 2006;12:5383–97. https://doi.org/10.1002/chem.200501639.Suche in Google Scholar PubMed

147. Bassan, A, Zou, W, Reyes, E, Himo, F, C´ordova, A. The origin of stereoselectivity in primary amino acid catalyzed intermolecular aldol reactions. Angew Chem Int Ed 2005;44:7028–32. https://doi.org/10.1002/anie.200502388.Suche in Google Scholar PubMed

148. Jiang, Z, Liang, Z, Wu, X, Lu, Y. Asymmetric aldol reactions catalyzed by tryptophan in water. Chem Commun 2006;14:2801–3. https://doi.org/10.1039/b606154k.Suche in Google Scholar PubMed

149. Amedjkouh, M. Aqua-organocatalyzed direct asymmetric Aldol reaction with acyclic amino acids and organic bases with control of diastereo- and enantioselectivity. Tetrahedron Asymmetry 2007;18:390–5. https://doi.org/10.1016/j.tetasy.2007.01.025.Suche in Google Scholar

150. Ramasastry, SSV, Zhang, H, Tanaka, F, Barbas, CFIII. Direct catalytic asymmetric synthesis of anti-1,2-amino alcohols and syn-1,2-diols through organocatalytic anti- mannich and syn-aldol reaction. J Am Chem Soc 2007;129:288–9. https://doi.org/10.1021/ja0677012.Suche in Google Scholar PubMed

151. Samanta, S, Zhao, C. Organocatalytic enantioselective synthesis of α-hydroxy phosphonates. J Am Chem Soc 2006;128:7442–3. https://doi.org/10.1021/ja062091r.Suche in Google Scholar PubMed PubMed Central

152. Dodda, R, Zhao, C. Organocatalytic highly enantioselective synthesis of secondary α-hydroxyphosphonates. Org Lett 2006;8:4911–4. https://doi.org/10.1021/ol062005s.Suche in Google Scholar PubMed PubMed Central

153. He, L, Tang, Z, Cun, L-F, Mi, A-Q, Jiang, Y-Z, Gong, L-Z. L-Proline amide-catalyzed direct asymmetric aldol reaction of aldehydes with chloroacetone. Tetrahedron 2006;62:346–51. https://doi.org/10.1016/j.tet.2005.09.061.Suche in Google Scholar

154. Xie, H, Zhang, S, Li, H, Zhang, X, Zhao, S, Xu, Z, et al.. Total synthesis of polyene natural product dihydroxerulin by mild organocatalyzed dehydrogenation of alcohols. Chem Eur J 2012;18:2230–4. https://doi.org/10.1002/chem.201103325.Suche in Google Scholar PubMed

155. Li, H, Wang, J, E-Nunu, T, Zu, L, Jiang, W, Wei, S, et al.. One-pot approach to chiral chromenes via enantioselective organocatalytic domino oxa-Michael–Aldol reaction. Chem Commun 2007;7:507–9. https://doi.org/10.1039/b611502k.Suche in Google Scholar PubMed

156. Zhu, S, Yu, S, Ma, D. Highly efficient catalytic system for enantioselective Michael addition of aldehydes to nitroalkenes in water. Angew Chem Int Ed 2008;47:545–8. https://doi.org/10.1002/anie.200704161.Suche in Google Scholar PubMed

157. Zhao, GL, Xu, Y, Sundén, H, Eriksson, L, Sayah, M, Córdova, A. Organocatalytic enantioselective conjugate addition of aldehydes to maleimides. Chem Com 2007:734–5. https://doi.org/10.1039/b614962f.Suche in Google Scholar PubMed

158. Chimni, SS, Mahajan, D, Babu, VVS. Protonated chiral prolinamide catalyzed enantioselective direct aldol reaction in water. Tetrahedron Lett 2005;46:5617–9. https://doi.org/10.1016/j.tetlet.2005.06.112.Suche in Google Scholar

159. Chimni, SS, Mahajan, D. Small organic molecule catalyzed enantioselective direct aldol reaction in water. Tetrahedron Asymmetry 2006;17:2108–19. https://doi.org/10.1016/j.tetasy.2006.07.016.Suche in Google Scholar

160. Raj, M, Vishnumaya, GSK, Singh, VK. Highly enantioselective direct Aldol reaction catalyzed by organic molecules. Org Lett 2006;8:4097–9. https://doi.org/10.1021/ol0616081.Suche in Google Scholar PubMed

161. Tang, Z, Jiang, F, Yu, L-T, Cui, X, Gong, L-Z, Mi, A-Q, et al.. Novel small organic molecules for a highly enantioselective direct aldol reaction. J Am Chem Soc 2003;125:5262–3. https://doi.org/10.1021/ja034528q.Suche in Google Scholar PubMed

162. Tang, Z, Yang, Z-H, Chen, X-H, Cun, L-F, Mi, A-Q, Jiang, Y-Z, et al.. A highly efficient organocatalyst for direct aldol reactions of ketones with aldedydes. J Am Chem Soc 2005;127:9285–9. https://doi.org/10.1021/ja0510156.Suche in Google Scholar PubMed

163. Berkessel, A, Koch, B, Lex, J. Proline-derived N-sulfonylcarboxamides: readily available, highly enantioselective and versatile catalysts for direct aldol reactions. Adv Syn Cat 2004;346:1141–6. https://doi.org/10.1002/adsc.200404126.Suche in Google Scholar

164. Cobb, AJA, Shaw, DM, Longbottom, DA, Gold, JB, Ley, SV. Organocatalysis with proline derivatives: improved catalysts for the asymmetric mannich, nitro-michael and aldol reactions. Org Biomol Chem 2005;3:84–96. https://doi.org/10.1039/b414742a.Suche in Google Scholar PubMed

165. Meciarová, M, Toma, S, Berkessel, A, Koch, B. Enantioselective aldol reactions catalysed by N-toluenesulfonyl-L-proline amide in ionic liquids. Lett Org Chem 2006;3:437–41.10.2174/157017806777828402Suche in Google Scholar

166. Chen, JR, Lu, HH, Li, XY, Cheng, L, Wan, J, Xiao, WJ. Readily tunable and bifunctional L-prolinamide derivatives: design and application in the direct enantioselective aldol reactions. Org Lett 2005;7:4543–5. https://doi.org/10.1021/ol0520323.Suche in Google Scholar PubMed

167. Chen, JR, Li, XY, Xing, XN, Xiao, WJ. Sterically and electronically tunable and bifunctional organocatalysts: design and application in asymmetric aldol reaction of cyclic ketones with aldehydes. J Org Chem 2006;71:8198–202. https://doi.org/10.1021/jo0615089.Suche in Google Scholar PubMed

168. Wang, W, Li, H, Wang, J. Direct pyrrolidine sulfonamide promoted enantioselective Aldol reactions of α,α-dialkyl aldehydes: synthesis of quaternary carbon-containing β- hydroxy carbonyl compounds. Tetrahedron Lett 2005;46:5077–9. https://doi.org/10.1016/j.tetlet.2005.05.067.Suche in Google Scholar

169. Cao, C-L, Ye, M-C, Sun, X-L, Tang, Y. Pyrrolidine-thiourea as a bifunctional organocatalyst: highly enantioselective michael addition of cyclohexanone to nitroolefins. Org Lett 2006;8:2901–4. https://doi.org/10.1021/ol060481c.Suche in Google Scholar PubMed

170. Yan, ZY, Niu, YN, Wei, HL, Wu, LY, Zhao, YB, Liang, YM. Combining proline and “click chemistry”: a class of versatile organocatalysts for the highly diastereo- and enantioselective michael addition in water. Tetrahedron Asymmetry 2006;17:3288–93. https://doi.org/10.1016/j.tetasy.2006.12.003.Suche in Google Scholar

171. Russo, A, Botta, G, Lattanzi, A. Highly stereoselective direct Aldol reactions catalyzed by (S)-NOBIN-l-prolinamide. Tetrahedron 2007;63:11886–92. https://doi.org/10.1016/j.tet.2007.09.027.Suche in Google Scholar

172. Guizzetti, S, Benaglia, M, Pignataro, L, Puglisi, A. A multifunctional proline-based organic catalyst for enantioselective aldol reactions. Tetrahedron Asymmetry 2006;17:2754–60. https://doi.org/10.1016/j.tetasy.2006.10.018.Suche in Google Scholar

173. Guillena, G, Hita, MC. High acceleration of the direct aldol reaction cocatalyzed by BINAM-prolinamides and benzoic acid in aqueous media. Tetrahedron Asymmetry 2006;17:1493–7. https://doi.org/10.1016/j.tetasy.2006.05.026.Suche in Google Scholar

174. Guillena, G, Hita, MC, Nájera, C. BINAM-prolinamides as recoverable catalysts in the direct aldol condensation. Tetrahedron Asymmetry 2006;17:729–33. https://doi.org/10.1016/j.tetasy.2006.02.004.Suche in Google Scholar

175. Bradshaw, B, Etxebarria-Jardi, G, Bonjoch, J, Viózquez, SF, Guillena, G, Nájera, C. Efficient solvent-free robinson annulation protocols for the highly enantioselective synthesis of the wieland-miescher ketone and analogues. Adv Synth Catal 2009;351:2482–90. https://doi.org/10.1002/adsc.200900321.Suche in Google Scholar

176. Guillena, G, Hita, MC, Na´jera, C. High acceleration of the direct Aldol reaction cocatalyzed by BINAM-prolinamides and benzoic acid in aqueous media. Tetrahedron Asymmetry 2008;17:1493–7.10.1016/j.tetasy.2006.05.026Suche in Google Scholar

177. Gorres, KL, Raines, RT. Prolyl 4-hydroxylase. Crit Rev Biochem Mol Biol 2010;45:106–24. https://doi.org/10.3109/10409231003627991.Suche in Google Scholar

178. Itagaki, N, Iwabuchi, Y. Enantio- and diastereocontrolled synthesis of (+)-juvabione employing organocatalytic desymmetrisation and photoinduced fragmentation. Chem Commun 2007;12:1175–6. https://doi.org/10.1039/b616641e.Suche in Google Scholar

179. Hayashi, Y, Sumiya, T, Takahashi, J, Gotoh, H, Urushima, T, Shoji, M. Highly diastereo- and enantioselective direct aldol reactions in water. Angew Chem Int Ed 2006;45:958–61. https://doi.org/10.1002/anie.200502488.Suche in Google Scholar

180. Hayashi, Y, Aratake, S, Okano, T, Takahashi, J, Sumiya, T, Shoji, M. Combined proline- surfactant organocatalyst for the highly diastereo- and enantioselective aqueous direct cross-Aldol reaction of aldehydes. Angew Chem Int Ed 2006;45:5527–9. https://doi.org/10.1002/anie.200601156.Suche in Google Scholar

181. Zhong, L, Gao, Q, Gao, J, Xiao, J, Li, C. Direct catalytic asymmetric aldol reactions on chiral catalysts assembled in the interface of emulsion droplets. J Catal 2007;250:360–4. https://doi.org/10.1016/j.jcat.2007.06.017.Suche in Google Scholar

182. Fache, F, Piva, O. Synthesis and applications of the first polyfluorous proline derivative. Tetrahedron Asymmetry 2003;14:139–43. https://doi.org/10.1016/s0957-4166(02)00796-6.Suche in Google Scholar

183. Shen, Z, Chen, W, Jiang, H, Ding, Y, Luo, X, Zhang, Y. Direct asymmetric Aldol reactions catalyzed by (4R)-4-(β-naphthalenyl) methoxy-(S)-proline. Chirality 2005;17:119–20. https://doi.org/10.1002/chir.20107.Suche in Google Scholar PubMed

184. Bellis, E, Kokotos, G. 4-Substituted prolines as organocatalysts for Aldol reactions. Tetrahedron 2005;61:8669–76. https://doi.org/10.1016/j.tet.2005.06.113.Suche in Google Scholar

185. Luo, H, Yan, X, Chen, L, Li, Y, Liu, N, Yin, G. Enantioselective catalytic domino aza- michael-henry reactions: one-pot asymmetric synthesis of 3-nitro-1,2- dihydroquinolines via iminium activation. Eur J Org Chem 2016:1702–7. https://doi.org/10.1002/ejoc.201501618.Suche in Google Scholar

186. Dan-Qian Xu, D-Q, Wang, Y-F, Luo, S-P, Zhang, S, Zhong, A-G, Chen, H, et al.. A Novel enantioselective catalytic tandem oxa-michael–henry reaction: one-Pot organocatalytic asymmetric synthesis of 3-nitro-2H-chromenes. Adv Synth Catal 2008;350:2610–6. https://doi.org/10.1002/adsc.200800535.Suche in Google Scholar

187. Yin, G, Zhang, R, Lei, L, Tian, J, Chen, L. One-pot enantioselective synthesis of 3-nitro-2H-chromenes catalyzed by a simple 4-hydroxyprolinamide with 4- nitrophenol as co-catalyst. Eur J Org Chem 2013;45:5431–8. https://doi.org/10.1002/ejoc.201300505.Suche in Google Scholar

188. Itoh, T, Ishikawa, H, Hayashi, Y. Asymmetric Aldol reaction of acetaldehyde and isatin derivatives for the total syntheses of ent-convolutamydine E and CPC-1 and a half fragment of madindoline A and B. Org Lett 2009;11:3854–7. https://doi.org/10.1021/ol901432a.Suche in Google Scholar PubMed

189. Bhowmick, S, Kunte, SS, Bhowmick, KC. A new organocatalyst derived from abietic acid and 4-hydroxy-L-proline for direct asymmetric Aldol reactions in aqueous media. Tetrahedron Asymmetry 2014;25:1292–7. https://doi.org/10.1016/j.tetasy.2014.07.012.Suche in Google Scholar

190. Itagaki, N, Kimura, M, Sugahara, T, Iwabuchi, Y. Expedient synthesis of potent cannabinoid receptor Agonist (-)-CP55,940. Org Lett 2005;7:4181–3. https://doi.org/10.1021/ol051570c.Suche in Google Scholar PubMed