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

…, P Majer, E Majerová, TA Guerassina, MA Eissenstat

Index: Smrcina, Martin; Majer, Pavel; Majerova, Eva; Guerassina, Tatiana A.; Eissenstat, Michael A. Tetrahedron, 1997 , vol. 53, # 38 p. 12867 - 12874

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Citation Number: 73

Abstract

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 ...