Facile stereoselective synthesis of γ-substituted γ-amino acids from the corresponding α-amino acids

A facile stereoselective method for the synthesis of γ-substituted, γ-amino acids from α-amino acids was developed. The key step of the procedure is complete reduction of the keto functionality of α-amino acyl Meldrum's acid by sodium acetoxyborohydride. The resulting amino alkyl Meldrum's...

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Bibliographic Details
Published inTetrahedron Vol. 53; no. 38; pp. 12867 - 12874
Main Authors Smrcina, Martin, Majer, Pavel, Majerová, Eva, Guerassina, Tatiana A., Eissenstat, Michael A.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 22.09.1997
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SODIUM
INHIBITION
PEPSTATIN
ANALOGS
GLUTAMATE
PEPSIN
CYTOCHALASAN SYNTHESIS
DERIVATIVES
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Summary:A facile stereoselective method for the synthesis of γ-substituted, γ-amino acids from α-amino acids was developed. The key step of the procedure is complete reduction of the keto functionality of α-amino acyl Meldrum's acid by sodium acetoxyborohydride. The resulting amino alkyl Meldrum's acid undergoes thermal decarboxylative ring closure to a 5-substituted pyrrolidinone which yields the corresponding γ-amino acid after basic hydrolysis. The overall yield of the procedure ranges from 40 to 65%.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)00840-5