Home Organo-catalysis as emerging tools in organic synthesis: aldol and Michael reactions
Article
Licensed
Unlicensed Requires Authentication

Organo-catalysis as emerging tools in organic synthesis: aldol and Michael reactions

  • Nagaraju Kerru , Suresh Maddila EMAIL logo and Sreekantha B. Jonnalagadda
Published/Copyright: January 5, 2022
Become an author with De Gruyter Brill
Submit Manuscript Author Information
Physical Sciences Reviews
From the journal Physical Sciences Reviews Volume 7 Issue 4-5

Abstract

Organocatalysis has occupied sustainable position in organic synthesis as a powerful tool for the synthesis of enantiomeric-rich compounds with multiple stereogenic centers. Among the various organic molecules for organocatalysis, the formation of carbon–carbon is viewed as a challenging issue in organic synthesis. The asymmetric aldol and Michael addition reactions are the most significant methods for C–C bond forming reactions. These protocols deliver a valuable path to access chiral molecules, which are useful synthetic hybrids in biologically potent candidates and desirable versatile pharmaceutical intermediates. This work highlighted the impact of organocatalytic aldol and Michael addition reactions in abundant solvent media. It focused on the crucial methods to construct valuable molecules with high enantio- and diastereo-selectivity.

Keywords: aldol; asymmetric synthesis; enantioselectivity; Michael addition; organocatalysis
Corresponding author: Dr. Suresh Maddila, Department of Chemistry, GITAM Institute of Sciences, GITAM University, Gandhi Nagar, Rushikonda, Visakhapatnam, Andhra Pradesh-530045, India; and School of Chemistry & Physics, University of KwaZulu-Natal, Westville Campus, Chiltern Hills, Durban-4000, South Africa, E-mail:

Funding source: GITAM University

Award Identifier / Grant number: (30-456/2018(BSR))

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: The authors are grateful to the GITAM Deemed to be University (Award ID (30-456/2018(BSR))), Bengaluru and Visakhapatnam, India, for financial and research support.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

1. Han, B, He, XH, Liu, YQ, He, G, Peng, C, Li, JL. Asymmetric organocatalysis: an enabling technology for medicinal chemistry. Chem Soc Rev 2021;50:1522–86. https://doi.org/10.1039/d0cs00196a.Search in Google Scholar PubMed

2. Zhan, G, Du, W, Chen, YC. Switchable divergent asymmetric synthesis via organocatalysis. Chem Soc Rev 2017;46:1675–92. https://doi.org/10.1039/c6cs00247a.Search in Google Scholar PubMed

3. Lassaletta, JM. Spotting trends in organocatalysis for the next decade. Nat Commun 2020;11:3787–891. https://doi.org/10.1038/s41467-020-17600-y.Search in Google Scholar PubMed PubMed Central

4. Chevis, PJ, Pyne, SG. Synthesis of enantioenriched α-heteroatom functionalized aldehydes by chiral organocatalysis and their synthetic applications. Org Chem Front 2021;8:2287–314. https://doi.org/10.1039/d1qo00101a.Search in Google Scholar

5. List, B. Introduction: organocatalysis. Chem Rev 2007;107:5413–5. https://doi.org/10.1021/cr078412e.Search in Google Scholar

6. Maruoka, K, List, B, Yamamoto, H, Gong, LZ. Organocatalysis: a web collection. Chem Commun 2012;48:10703. https://doi.org/10.1039/c2cc90327j.Search in Google Scholar PubMed

7. Hernandez, JG, Juaristi, E. Recent efforts directed to the development of more sustainable asymmetric organocatalysis. Chem Commun 2012;48:5396–409. https://doi.org/10.1039/c2cc30951c.Search in Google Scholar PubMed

8. Bhowmick, S, Bhowmick, KC. Catalytic asymmetric carbon-carbon bond-forming reactions in aqueous media. Tetrahedron: Asymmetry 2011;22:1945–79. https://doi.org/10.1016/j.tetasy.2011.11.009.Search in Google Scholar

9. Raj, M, Singh, VK. Organocatalytic reactions in water. Chem Commun 2009;2009:6687–703. https://doi.org/10.1039/b910861k.Search in Google Scholar PubMed

10. Vogel, P, Lam, Y, Simon, A, Houk, KN. Organocatalysis: fundamentals and comparisons to metal and enzyme catalysis. Catalysts 2016;6:128. https://doi.org/10.3390/catal6090128.Search in Google Scholar

11. Chen, DF, Han, ZY, Zhou, XL, Gong, LZ. Asymmetric organocatalysis combined with metal catalysis: concept, proof of concept, and beyond. Acc Chem Res 2014;47:2365–77. https://doi.org/10.1021/ar500101a.Search in Google Scholar PubMed

12. Ruiz-Olalla, A, Retamosa, MG, Cossio, FP. Densely substituted l-proline esters as catalysts for asymmetric Michael additions of ketones to nitroalkenes. J Org Chem 2015;80:5588–99. https://doi.org/10.1021/acs.joc.5b00495.Search in Google Scholar PubMed

13. Ruiz-Olalla, A, Würdemann, MA, Wanner, MJ, Ingemann, S, van Maarseveen, JH, Hiemstra, H. Organocatalytic enantioselective Pictet-Spengler approach to biologically relevant 1-benzyl-1,2,3,4-tetrahydroisoquinoline alkaloids. J Org Chem 2015;80:5125–32. https://doi.org/10.1021/acs.joc.5b00509.Search in Google Scholar PubMed

14. Bae, HY, Song, CE. Unprecedented hydrophobic amplification in noncovalent organocatalysis “on water”: hydrophobic chiral squaramide catalyzed Michael addition of malonates to nitroalkenes. ACS Catal 2015;5:3613–9. https://doi.org/10.1021/acscatal.5b00685.Search in Google Scholar

15. Boeckman, RK, Biegasiewicz, KF, Tusch, DJ, Miller, JR. Organocatalytic enantioselective α-hydroxymethylation of aldehydes: mechanistic aspects and optimization. J Org Chem 2015;80:4030–45. https://doi.org/10.1021/acs.joc.5b00380.Search in Google Scholar PubMed

16. Bonne, D, Constantieux, T, Coquerel, Y, Rodriguez, J. Asymmetric organocascades involving the formation of two C–heteroatom bonds from two distinct heteroatoms. Org Biomol Chem 2012;10:3969–73. https://doi.org/10.1039/c2ob25248a.Search in Google Scholar PubMed

17. Das, U, Huang, CH, Lin, W. Enantioselective synthesis of substituted pyrans via amine-catalyzed Michael addition and subsequent enolization/cyclisation. Chem Commun 2012;48:5590–2. https://doi.org/10.1039/c2cc31445b.Search in Google Scholar PubMed

18. Duce, S, Mateo, A, Alonso, I, Luis, J, Ruano, G, Cid, MB. Role of quaternary ammonium salts as new additives in the enantioselective organocatalytic β-benzylation of enals. Chem Commun 2012;48:5184–6. https://doi.org/10.1039/c2cc31451g.Search in Google Scholar PubMed

19. Oliveira, VG, Cardoso, MFC, Forezi, LSM. Organocatalysis: a brief overview on its evolution and applications. Catalysts 2018;8:605. https://doi.org/10.3390/catal8120605.Search in Google Scholar

20. Page, PCB, Mace, A, Arquier, D, Bethell, D, Buckley, BR, Willock, DJ, et al.. Towards heterogeneous organocatalysis: chiral iminium cations supported on porous materials for enantioselective alkene epoxidation. Catal Sci Technol 2013;3:2330–9. https://doi.org/10.1039/c3cy00352c.Search in Google Scholar

21. Nguyen, TN, Chen, PA, Setthakarn, K, May, JA. Chiral diol-based organocatalysts in enantioselective reactions. Molecules 2018;23:2317. https://doi.org/10.3390/molecules23092317.Search in Google Scholar PubMed PubMed Central

22. Klare, H, Neudorfl, JM, Goldfuss, B. New hydrogen-bonding organocatalysts: Chiral cyclophosphazanes and phosphorus amides as catalysts for asymmetric Michael additions. Beilstein J Org Chem 2014;10:224–36. https://doi.org/10.3762/bjoc.10.18.Search in Google Scholar PubMed PubMed Central

23. Phillips, AMF, Prechtl, MHG, Pombeiro, AJL. Non-covalent interactions in enantioselective organocatalysis: theoretical and mechanistic studies of reactions mediated by dual H-bond donors, bifunctional squaramides, thioureas and related catalysts. Catalysts 2021;11:569. https://doi.org/10.3390/catal11050569.Search in Google Scholar

24. Gimeno, MC, Herrera, RP. Hydrogen bonding networks in chiral thiourea organocatalysts: evidence on the importance of the aminoindanol moiety. Cryst Growth Des 2016;16:5091–9. https://doi.org/10.1021/acs.cgd.6b00683.Search in Google Scholar

25. Jusseau, X, Chabaud, L, Guillou, C. Synthesis of γ-butenolides and α,β-unsaturated γ-butyrolactams by addition of vinylogous nucleophiles to Michael acceptors. Tetrahedron 2014;70:2595–615. https://doi.org/10.1016/j.tet.2014.01.057.Search in Google Scholar

26. Heravi, MM, Zadsirjan, V, Dehghani, M, Hosseintash, N. Current applications of organocatalysts in asymmetric aldol reactions: an update. Tetrahedron: Asymmetry 2017;28:587–707. https://doi.org/10.1016/j.tetasy.2017.04.006.Search in Google Scholar

27. Bhowmick, S, Mondal, A, Ghosh, A, Bhowmick, KC. Water: the most versatile and nature’s friendly media in asymmetric organocatalyzed direct aldol reactions. Tetrahedron: Asymmetry 2015;26:1215–44. https://doi.org/10.1016/j.tetasy.2015.09.009.Search in Google Scholar

28. Heravi, MM, Asadi, S. Recent applications of organocatalysts in asymmetric aldol reactions. Tetrahedron: Asymmetry 2012;23:1431–65. https://doi.org/10.1016/j.tetasy.2012.10.002.Search in Google Scholar

29. Yamashita, Y, Yasukawa, T, Yoo, WJ, Kitanosono, T, Kobayashi, S. Catalytic enantioselective aldol reactions. Chem Soc Rev 2018;47:4388–480. https://doi.org/10.1039/c7cs00824d.Search in Google Scholar PubMed

30. Andre, JC, Bock, MC, Hofner, G, Wanner, KT. Synthesis and biological evaluation of α- and β-hydroxy substituted amino acid derivatives as potential mGAT1–4 inhibitors. Med Chem Res 2020;29:1321–40. https://doi.org/10.1007/s00044-020-02548-x.Search in Google Scholar

31. Lefranc, A, Gremaud, L, Alexakis, A. Construction of bicyclo[3.2.1]octanes with four stereogenic centers by organocatalytic domino Michael/aldol reaction. Org Lett 2014;16:5242–5. https://doi.org/10.1021/ol502171h.Search in Google Scholar

32. Guevara-Pulido, JO, Andres, JM, Pedrosa, R. The organocatalyzed domino Michael-aldol reaction revisited synthesis of enantioenriched 3-hydroxycyclohexanone derivatives by reaction of enals with α,α′-diaryl-substituted acetone. RSC Adv 2015;5:65975–81. https://doi.org/10.1039/c5ra11215j.Search in Google Scholar

33. Wurtz, CA. Aldol condensation. Bull Soc Chim Fr 1872;17:436–42.Search in Google Scholar

34. Hong, BC, Nimje, RY, Sadani, AA, Liao, JH. Organocatalytic enantioselective domino Michael-aldol condensation of 5-oxoalkanal and α,β-unsaturated aldehydes. efficient assembly of densely functionalized cyclohexenes. Org Lett 2008;10:2345–8. https://doi.org/10.1021/ol8005369.Search in Google Scholar

35. Gryko, D, Saletra, WJ. Organocatalytic asymmetric aldol reaction in the presence of water. Org Biomol Chem 2007;5:2148–53. https://doi.org/10.1039/b703254d.Search in Google Scholar

36. Braun, M, Devant, R. (R)- and (S)-2-acetoxy-1,1,2-triphenylethanol - effective synthetic equivalents of a chiral acetate enolate. Tetrahedron Lett 1984;25:5031–4. https://doi.org/10.1016/s0040-4039(01)91110-4.Search in Google Scholar

37. Jacoby, CG, Vontobel, PHV, Bach, MF, Schneider, PH. Highly efficient organocatalysts for the asymmetric aldol reaction. New J Chem 2018;42:7416–21. https://doi.org/10.1039/c7nj04424k.Search in Google Scholar

38. Kanemitsu, TT, Umehara, A, Miyazaki, M, Nagata, K, Itoh, T. L-t-Leucine-catalyzed direct asymmetric aldol reaction of cyclic ketones. Eur J Org Chem 2011;2011:993–7. https://doi.org/10.1002/ejoc.201001413.Search in Google Scholar

39. Houk, KN, Cheong, PHY. Computational prediction of small-molecule catalysts. Nature 2008;455:309–13. https://doi.org/10.1038/nature07368.Search in Google Scholar PubMed PubMed Central

40. Wu, C, Fu, X, Li, S. Highly efficient, large-scale, asymmetric direct aldol reaction employing simple threonine derivatives as recoverable organocatalysts in the presence of water. Eur J Org Chem 2011;2011:1291–9. https://doi.org/10.1002/ejoc.201001396.Search in Google Scholar

41. Guo, Q, Zhao, JCG. Primary amine catalyzed aldol reaction of isatins and acetaldehyde. Tetrahedron Lett 2012;53:1768–71. https://doi.org/10.1016/j.tetlet.2012.01.108.Search in Google Scholar

42. Perera, S, Naganaboina, VK, Wang, L, Zhang, B, Guo, QS, Rout, L, et al.. Organocatalytic high enantioselective synthesis of β-Formyl-α-hydroxyphosphonates. Adv Synth Catal 2011;353:1729–34. https://doi.org/10.1002/adsc.201000835.Search in Google Scholar PubMed PubMed Central

43. Wynands, L, Delacroix, S, Nhien, ANV, Soriano, E, Contelles, JM, Postel, D. New glycosyl-a-aminotetrazole-based catalysts for highly enantioselective aldol reactions. Tetrahedron 2013;69:4899–907. https://doi.org/10.1016/j.tet.2013.04.043.Search in Google Scholar

44. Shim, JH, Kim, MJ, Lee, JY, Kim, KH, Ha, DC. Organocatalytic asymmetric aldol reaction using protonated chiral 1,2-diamines. Tetrahedron Lett 2020;61:152295. https://doi.org/10.1016/j.tetlet.2020.152295.Search in Google Scholar

45. Zong, H, Huang, H, Bian, G, Song, L. Fine-tuning the structures of chiral diamine ligands in the catalytic asymmetric aldol reactions of trifluoromethyl aromatic ketones with linear aliphatic ketones. J Org Chem 2014;79:11768–73. https://doi.org/10.1021/jo5022103.Search in Google Scholar PubMed

46. Li, L, Gou, S, Liu, F. Highly stereoselective direct aldol reactions catalyzed by a bifunctional chiral diamine. Tetrahedron: Asymmetry 2014;25:193–7. https://doi.org/10.1016/j.tetasy.2013.11.017.Search in Google Scholar

47. Hernandez, JG, Garcia-Liopez, V, Juaristi, E. Solvent-free asymmetric aldol reaction organocatalyzed by (S)-proline-containing thiodipeptides under ball-milling conditions. Tetrahedron 2012;68:92–7. https://doi.org/10.1016/j.tet.2011.10.093.Search in Google Scholar

48. List, B, Lerner, RA, Barbas, CF. Proline-catalyzed direct asymmetric aldol reactions. J Am Chem Soc 2000;122:2395–6. https://doi.org/10.1021/ja994280y.Search in Google Scholar

49. Sakthivel, K, Notz, W, Bui, T, Barbas, CF. 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.Search in Google Scholar PubMed

50. Pihko, PM, Laurikainen, KM, Usano, A, Nyberg, A, Kaavi, JA. Effect of additives on the prolinecatalyzed ketone–aldehyde aldol reactions. Tetrahedron 2006;62:317–32. https://doi.org/10.1016/j.tet.2005.09.070.Search in Google Scholar

51. 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.Search in Google Scholar PubMed

52. Northrup, AB, MacMillan, DWC. The first direct and enantioselective cross-aldol reaction of aldehydes. J Am Chem Soc 2002;124:6798–9. https://doi.org/10.1021/ja0262378.Search in Google Scholar

53. Mangion, IK, Northrup, AB, MacMillan, DWC. The Importance of iminium geometry control in enamine catalysis: identification of a new catalyst architecture for aldehydealdehyde couplings. Angew Chem Int Ed 2004;48:6890–2. https://doi.org/10.1002/ange.200461851.Search in Google Scholar

54. Bhati, M, Kumari, K, Easwar, S. Probing the synergistic catalytic model: a rationally designed urea-tagged proline catalyst for the direct asymmetric aldol reaction. J Org Chem 2018;83:8225–32. https://doi.org/10.1021/acs.joc.8b00962.Search in Google Scholar

55. Han, MY, Xie, X, Zhou, D, Li, P, Wang, L. Organocatalyzed direct aldol reaction of silyl glyoxylates for the synthesis of α-hydroxysilanes. Org Lett 2017;19:2282–5. https://doi.org/10.1021/acs.orglett.7b00811.Search in Google Scholar

56. Cho, E, Kim, TH. Direct asymmetric aldol reaction co-catalyzed by L-proline and isothiouronium salts. Tetrahedron Lett 2014;55:6470–3. https://doi.org/10.1016/j.tetlet.2014.10.009.Search in Google Scholar

57. Castaneda, AM, Solla, HR, Concellon, C, del-Amo, V. Switching diastereoselectivity in proline-catalyzed aldol reactions. J Org Chem 2012;77:10375–81. https://doi.org/10.1021/jo3020352.Search in Google Scholar

58. Thorat, PB, Goswami, SV, Sondankar, VP, Bhusare, SR. Stereoselective synthesis of vic-halohydrins and unusual Knoevenagel product from an organocatalyzed aldol reaction: a non-enamine mode. Chinese J Catal 2015;36:1093–100. https://doi.org/10.1016/s1872-2067(14)60317-x.Search in Google Scholar

59. Thorat, PB, Goswami, SV, Magar, RL, Patil, BR, Bhusare, SR. An efficient organocatalysis: a one‐pot highly enantioselective synthesis of α‐amino phosphonates. Eur J Org Chem 2013;2013:5509–16. https://doi.org/10.1002/ejoc.201300494.Search in Google Scholar

60. Thorat, PB, Goswami, SV, Jadhav, WN, Bhusare, SR. Water-assisted organocatalysis: an enantioselective green protocol for the henry reaction. Aust J Chem 2013;66:661–6. https://doi.org/10.1071/ch12428.Search in Google Scholar

61. Vamisetti, GB, Chowdhury, R, Ghosh, SK. Organocatalytic decarboxylative aldol reaction of β-ketoacids with α-ketophosphonates en route for the enantioselective synthesis of tertiary α-hydroxyphosphonates. Org Biomol Chem 2017;15:3869–73. https://doi.org/10.1039/c7ob00796e.Search in Google Scholar PubMed

62. Sakai, T, Hirashima, S, Matsushima, Y, Nakano, T, Ishii, D, Yamashita, Y, et al.. Synthesis of chiral γ,γ-disubstituted γ-butenolides via direct vinylogous aldol reaction of substituted furanone derivatives with aldehydes. Org Lett 2019;21:2606–9. https://doi.org/10.1021/acs.orglett.9b00574.Search in Google Scholar PubMed

63. Park, JH, Sim, JH, Song, CE. Direct access to β-trifluoromethyl-β-hydroxy thioesters by biomimetic organocatalytic enantioselective aldol reaction. Org Lett 2019;21:4567–70. https://doi.org/10.1021/acs.orglett.9b01469.Search in Google Scholar PubMed

64. Moles, FJN, Guillena, G, Najera, C. Aqueous organocatalyzed aldol reaction of glyoxylic acid for the enantioselective synthesis of α-hydroxy-γ-keto acids. RSC Adv 2014;4:9963–6. https://doi.org/10.1039/c3ra46800c.Search in Google Scholar

65. Konda, S, Guo, QS, Abe, M, Huang, H, Arman, H, Zhao, JCG. Organocatalyzed asymmetric aldol reactions of ketones and β,γ-unsaturated α-ketoesters and phenylglyoxal hydrates. J Org Chem 2015;80:806–15. https://doi.org/10.1021/jo502254e.Search in Google Scholar PubMed

66. Tsogoeva, SB. Recent advances in asymmetric organocatalytic 1,4-conjugate additions. Eur J Org Chem 2007;2007:1701–16. https://doi.org/10.1002/ejoc.200600653.Search in Google Scholar

67. Roca-Lopez, D, Sadaba, D, Delso, I, Herrera, RP, Tejero, T, Merino, P. Asymmetric organocatalytic synthesis of c-nitrocarbonyl compounds through Michael and domino reactions. Tetrahedron: Asymmetry 2010;21:2561–601. https://doi.org/10.1016/j.tetasy.2010.11.001.Search in Google Scholar

68. Bera, K, Ayyagari, N, Satam, N, Namboothiri, INN. Stereoselective synthesis of hydrazinodihydrofurans via cascade Michael addition–substitution involving the reaction of curcumin and other β-dicarbonyls with α-hydrazinonitroalkenes. Org Biomol Chem 2020;18:140–53. https://doi.org/10.1039/c9ob01974j.Search in Google Scholar PubMed

69. Reddy, SN, Reddy, VR, Dinda, S, Nanubolu, JB, Chandra, R. Asymmetric reaction of p-quinone diimide: organocatalyzed Michael addition of α-cyanoacetates. Org Lett 2018;20:2572–5. https://doi.org/10.1021/acs.orglett.8b00771.Search in Google Scholar PubMed

70. Huang, X, David, E, Jubault, P, Besset, T, Bonnaire, SC. Organocatalyzed sulfa-Michael addition of thiophenols on trisubstituted α-fluoroacrylates, a straightforward access to chiral fluorinated compounds. J Org Chem 2020;85:14055–67. https://doi.org/10.1021/acs.joc.0c02081.Search in Google Scholar PubMed

71. Zhou, XJ, Zhao, JQ, Chen, XM, Zhuo, JR, Zhang, YP, Chen, YZ, et al.. Organocatalyzed asymmetric dearomative aza-Michael/Michael addition cascade of 2-nitrobenzofurans and 2-nitrobenzothiophenes with 2-aminochalcones. J Org Chem 2019;84:4381–91. https://doi.org/10.1021/acs.joc.9b00401.Search in Google Scholar PubMed

72. Chen, S, Wang, Y, Zhou, Z. Organocatalyzed asymmetric Michael addition of 1-acetylindolin-3-ones to β,γ-unsaturated α-ketoesters: an access to chiral indolin-3-ones with two adjacent tertiary stereogenic centers. J Org Chem 2016;81:11432–8. https://doi.org/10.1021/acs.joc.6b02070.Search in Google Scholar PubMed

73. Gupta, V, Singh, RP. Enantioselective vinylogous Michael addition of α,β-unsaturated butenolide to 2-iminochromenes. New J Chem 2019;43:9771–5. https://doi.org/10.1039/c9nj01584a.Search in Google Scholar

74. Chowdhury, R, Kumar, M, Ghosh, SK. Organocatalyzed enantioselective Michael addition/cyclization cascade reaction of 3-isothiocyanato oxindoles with arylidene malonates. Org Biomol Chem 2016;14:11250–60. https://doi.org/10.1039/c6ob02104b.Search in Google Scholar PubMed

75. Wang, ZH, Wu, ZJ, Yue, DF, You, Y, Xu, XY, Zhang, XM, et al.. Enantioselective synthesis of chiral α,β-unsaturated γ-substituted butyrolactams by organocatalyzed direct asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam to 2-enoylpyridines. Org Biomol Chem 2016;14:6568–76. https://doi.org/10.1039/c6ob01191h.Search in Google Scholar PubMed

76. Luo, Y, Xie, KX, Yue, DF, Zhang, XM, Xu, XY, Yuan, WC. Organocatalytic asymmetric Michael addition of pyrazoleamides to β-phthalimidonitroethene. Tetrahedron 2017;73:6217–22. https://doi.org/10.1016/j.tet.2017.09.019.Search in Google Scholar
Received: 2021-08-26
Accepted: 2021-10-09
Published Online: 2022-01-05

© 2021 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. Editorial
  3. Organocatalysis: a green tool for sustainable developments
  4. Reviews
  5. Zwitterionic imidazolium salt: an effective green organocatalyst in synthetic chemistry
  6. The aryl iodine-catalyzed organic transformation via hypervalent iodine species generated in situ
  7. Baker’s yeast (Saccharomyces cerevisiae) catalyzed synthesis of bioactive heterocycles and some stereoselective reactions
  8. Critical trends in synthetic organic chemistry in terms of organocatalysis
  9. Organo-catalysis as emerging tools in organic synthesis: aldol and Michael reactions
  10. Synthetic drives for useful drug molecules through organocatalytic methods
  11. Organocatalytic total synthesis of bioactive compounds based on one-pot methodologies
  12. Organocatalysts based on natural and modified amino acids for asymmetric reactions
  13. Bronsted acidic surfactants: efficient organocatalysts for diverse organic transformations
  14. Microwave-induced biocatalytic reactions toward medicinally important compounds
  15. Sulfonated β-cyclodextrins: efficient supramolecular organocatalysts for diverse organic transformations
  16. Enzyme-catalyzed synthesis of bioactive heterocycles
https://doi.org/10.1515/psr-2021-0023
Keywords for this article
aldol; asymmetric synthesis; enantioselectivity; Michael addition; organocatalysis

Articles in the same Issue

  1. Frontmatter
  2. Editorial
  3. Organocatalysis: a green tool for sustainable developments
  4. Reviews
  5. Zwitterionic imidazolium salt: an effective green organocatalyst in synthetic chemistry
  6. The aryl iodine-catalyzed organic transformation via hypervalent iodine species generated in situ
  7. Baker’s yeast (Saccharomyces cerevisiae) catalyzed synthesis of bioactive heterocycles and some stereoselective reactions
  8. Critical trends in synthetic organic chemistry in terms of organocatalysis
  9. Organo-catalysis as emerging tools in organic synthesis: aldol and Michael reactions
  10. Synthetic drives for useful drug molecules through organocatalytic methods
  11. Organocatalytic total synthesis of bioactive compounds based on one-pot methodologies
  12. Organocatalysts based on natural and modified amino acids for asymmetric reactions
  13. Bronsted acidic surfactants: efficient organocatalysts for diverse organic transformations
  14. Microwave-induced biocatalytic reactions toward medicinally important compounds
  15. Sulfonated β-cyclodextrins: efficient supramolecular organocatalysts for diverse organic transformations
  16. Enzyme-catalyzed synthesis of bioactive heterocycles
Sign up now to receive a 20% welcome discount
Institutional Access
How does access work?
Have an idea on how to improve our website?
Please write us.
© 2025 De Gruyter Brill
Downloaded on 23.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/psr-2021-0023/html
Scroll to top button