Tetrahedron p. 12867 - 12874 (1997)
Update date:2022-08-03
Topics:
Smrcina, Martin
Majer, Pavel
Majerova, Eva
Guerassina, Tatiana A.
Eissenstat, Michael A.
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%.
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