Startseite Sila-Substitution of the α-Amino Acid Proline: Synthesis of rac- and (R)-4,4-Dimethyl-4-sila-proline Ethyl Ester
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Sila-Substitution of the α-Amino Acid Proline: Synthesis of rac- and (R)-4,4-Dimethyl-4-sila-proline Ethyl Ester

  • Vera Iris Handmann , Markus Merget und Reinhold Tacke EMAIL logo
Veröffentlicht/Copyright: 2. Juni 2014
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Zeitschrift für Naturforschung B
Aus der Zeitschrift Zeitschrift für Naturforschung B Band 55 Heft 2

Abstract In context with studies on silicon-containing α-amino acids and peptides, a strategy for the synthesis of the 4-sila-proline skeleton was developed. The synthesis of rac-and (R)-4,4-dimethyl-4-sila-proline ethyl ester [rac-2 and (R)-2] is described. Compounds rac-2 and (R)-2 (≥ 99% ee) were prepared by two-step syntheses, starting from 3,6-diethoxy-2,5-dihydro-pyrazine and (R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine, respectively.

Keywords : 4-Sila-proline Skeleton; 4,4-Dimethyl-4-sila-proline Ethyl Ester; a-Amino Acids; Asymmetrie Synthesis; Bioorganosilicon Chemistry
Received: 1999-10-26
Published Online: 2014-6-2
Published in Print: 2000-2-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Artikel in diesem Heft

  1. Sila-Substitution of the α-Amino Acid Proline: Synthesis of rac- and (R)-4,4-Dimethyl-4-sila-proline Ethyl Ester
  2. Synthesis and Crystal Structures of ATi[Nb6Cl18] Compounds (A = K, Rb, Cs, In, Tl)
  3. Optisch aktive Übergangsmetall-Komplexe, 122. Synthese von Palladium(II)-Schiff-Base-Komplexen -intramolekulare Wechselwirkungen / Optically Active Transition Metal Complexes, 122. Synthesis of Palladium (II) Complexes with Schiff Base Ligands -Intramolecular Interactions
  4. Intermetallic Cerium Compounds with Ordered U3Si2 Type Structure
  5. Electrochemical Synthesis of a 6-Coordinate Cadmium(II) Complex with N-Methylisatin N(4)-cyclohexylthiosemicarbazone
  6. Synthese und Kristallstruktur des Bromdifluormethyl-triphenyl- phosphoniumbromids, [(C6H5)3PCF2Br]+ Br- / Synthesis and Crystal Structure of Bromodifluoromethyl-triphenylphosphonium Bromide, [(C6H5)3PCF2Br]+ Br-
  7. Synthesis, Structure and Properties of Poly > [(N-(2-Hydroxyethyl)- N'-carboxymethyl-1,2-ethylenediamine-N, N'-Diacetato)copper(II) Hydrate], {[Cu(Hhedta)] · H2O }n
  8. Kristallstrukturen, Schwingungsspektren und Normalkoordinatenanalyse von cis-(n-Bu4N)2[ReBr4(NCS)2 ], cis-(n-Bu4N)2[ReBr4(NCSe)2] und cis-(n-Bu4N)2[ReBr4(NCS)(NCSe)] / Crystal Structures, Vibrational Spectra and Normal Coordinate Analyses of cis-(n-Bu4N)2[ReBr4(NCS)2], cis-(n-Bu4N)2[ReBr4(NCSe)2,] and cis -(n -Bu4N)2[ReBr4(NCS)(NCSe)]
  9. Bis(diphenylphosphanyl)amine and its Disulfide and Diselenide. Application of the INEPT-HEED Pulse Sequence for Measurement of 1J(31P, 15N) and Isotope Induced Chemical Shifts 1⊿ 14/15N(31P) at Natural Abundance of 15N
  10. Synthesis, Multinuclear (1H, 13C and 17O ) Magnetic Resonance Spectroscopy and Conformational Analysis of Some Substituted Aryl Naphthoates
  11. Substituent Influences on the Keto-Enol Tautomerism in 1-(2-Hydroxyphenyl)-3-α-and -β-naphthylpropane-1,3-diones Monitored by 1H and 13C NMR Spectroscopy
  12. Chiral Aryl Sulfonyl Hydantoins as Hypoglycemic Agents
  13. Endogenous Alkaloids in Man, Part 33. Dimethyl (2S,4S)-and (2R,4S)-5,5-Dimethyl-1,3-thiazolidine-2,4-dicarboxylates, Two Diastereomeric Glyoxylate-Derived Heterocycles
  14. The Inclusion of Carbon Disulfide in p-tert-Butylcalix[4]-and [6 ]arene - A Combined Crystallographic and Vibrational Spectroscopic Study
  15. Facile Regioselective Synthesis of 1,2,6,8-Tetraazaspiro[4.4]nona-2,6-dien-9-ones
  16. A New Triterpenoidal Saponin from the Bark of Guaiacum officinale L.
  17. Alternative Method for the Preparation of 4,5-Ethylenedithio-1,3-dithiole-2- thione and Related Compounds
  18. A Diterpenoid with a New Modified Abietane Skeleton from Salvia palaestina
https://doi.org/10.1515/znb-2000-0201
Schlagwörter für diesen Artikel
4-Sila-proline Skeleton; 4,4-Dimethyl-4-sila-proline Ethyl Ester; a-Amino Acids; Asymmetrie Synthesis; Bioorganosilicon Chemistry

Artikel in diesem Heft

  1. Sila-Substitution of the α-Amino Acid Proline: Synthesis of rac- and (R)-4,4-Dimethyl-4-sila-proline Ethyl Ester
  2. Synthesis and Crystal Structures of ATi[Nb6Cl18] Compounds (A = K, Rb, Cs, In, Tl)
  3. Optisch aktive Übergangsmetall-Komplexe, 122. Synthese von Palladium(II)-Schiff-Base-Komplexen -intramolekulare Wechselwirkungen / Optically Active Transition Metal Complexes, 122. Synthesis of Palladium (II) Complexes with Schiff Base Ligands -Intramolecular Interactions
  4. Intermetallic Cerium Compounds with Ordered U3Si2 Type Structure
  5. Electrochemical Synthesis of a 6-Coordinate Cadmium(II) Complex with N-Methylisatin N(4)-cyclohexylthiosemicarbazone
  6. Synthese und Kristallstruktur des Bromdifluormethyl-triphenyl- phosphoniumbromids, [(C6H5)3PCF2Br]+ Br- / Synthesis and Crystal Structure of Bromodifluoromethyl-triphenylphosphonium Bromide, [(C6H5)3PCF2Br]+ Br-
  7. Synthesis, Structure and Properties of Poly > [(N-(2-Hydroxyethyl)- N'-carboxymethyl-1,2-ethylenediamine-N, N'-Diacetato)copper(II) Hydrate], {[Cu(Hhedta)] · H2O }n
  8. Kristallstrukturen, Schwingungsspektren und Normalkoordinatenanalyse von cis-(n-Bu4N)2[ReBr4(NCS)2 ], cis-(n-Bu4N)2[ReBr4(NCSe)2] und cis-(n-Bu4N)2[ReBr4(NCS)(NCSe)] / Crystal Structures, Vibrational Spectra and Normal Coordinate Analyses of cis-(n-Bu4N)2[ReBr4(NCS)2], cis-(n-Bu4N)2[ReBr4(NCSe)2,] and cis -(n -Bu4N)2[ReBr4(NCS)(NCSe)]
  9. Bis(diphenylphosphanyl)amine and its Disulfide and Diselenide. Application of the INEPT-HEED Pulse Sequence for Measurement of 1J(31P, 15N) and Isotope Induced Chemical Shifts 1⊿ 14/15N(31P) at Natural Abundance of 15N
  10. Synthesis, Multinuclear (1H, 13C and 17O ) Magnetic Resonance Spectroscopy and Conformational Analysis of Some Substituted Aryl Naphthoates
  11. Substituent Influences on the Keto-Enol Tautomerism in 1-(2-Hydroxyphenyl)-3-α-and -β-naphthylpropane-1,3-diones Monitored by 1H and 13C NMR Spectroscopy
  12. Chiral Aryl Sulfonyl Hydantoins as Hypoglycemic Agents
  13. Endogenous Alkaloids in Man, Part 33. Dimethyl (2S,4S)-and (2R,4S)-5,5-Dimethyl-1,3-thiazolidine-2,4-dicarboxylates, Two Diastereomeric Glyoxylate-Derived Heterocycles
  14. The Inclusion of Carbon Disulfide in p-tert-Butylcalix[4]-and [6 ]arene - A Combined Crystallographic and Vibrational Spectroscopic Study
  15. Facile Regioselective Synthesis of 1,2,6,8-Tetraazaspiro[4.4]nona-2,6-dien-9-ones
  16. A New Triterpenoidal Saponin from the Bark of Guaiacum officinale L.
  17. Alternative Method for the Preparation of 4,5-Ethylenedithio-1,3-dithiole-2- thione and Related Compounds
  18. A Diterpenoid with a New Modified Abietane Skeleton from Salvia palaestina
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