FACILE STEREOSELECTIVE SYNTHESIS OF GAMMA-SUBSTITUTED GAMMA-AMINO ACIDS FROM THE CORRESPONDING ALPHA-AMINO-ACIDS

Authors
SMRCINA M MAJER P MAJEROVA E GUERASSINA TA EISSENSTAT MA
Citation
M. Smrcina et al., FACILE STEREOSELECTIVE SYNTHESIS OF GAMMA-SUBSTITUTED GAMMA-AMINO ACIDS FROM THE CORRESPONDING ALPHA-AMINO-ACIDS, Tetrahedron, 53(38), 1997, pp. 12867-12874
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
38
Year of publication
1997
Pages
12867 - 12874
Database
ISI
SICI code
0040-4020(1997)53:38<12867:FSSOGG>2.0.ZU;2-0
Abstract
A facile stereoselective method for the synthesis of gamma-substituted , gamma-amino acids from alpha-amino acids was developed. The key step of the procedure is complete reduction of the keto functionality of a lpha-amino acyl Meldrum's acid by sodium acetoxyborohydride. The resul ting amino alkyl Meldrum's acid undergoes thermal decarboxylative ring closure to a 5-substituted pyrrolidinone which yields, the correspond ing gamma-amino acid after basic hydrolysis. The overall yield of the procedure ranges from 40 to 65%. (C) 1997 Elsevier Science Ltd.