Towards the stereoselective synthesis of alpha-methylated (2S,3aS,7aS)-octahydroindole-2-carboxylic acid.
A high yielding and remarkably stereoselective alpha-methylation reaction of the (2S,3aS,7aS) stereoisomer of octahydroindole-2-carboxylic acid, (S,S,S)-Oic, suitably protected is described. The severe steric hindrance imposed by the fused cyclohexane ring, which prevents the application of Seebach's self-reproduction of chirality methodology, accounts for the formation of (S,S,S)-(alphaMe)Oic with high selectivity and retention of configuration.
Sayago
Francisco J
FJ
Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragón, Universidad de Zaragoza-CSIC, 50009 Zaragoza, Spain.
Calaza
M Isabel
MI
Jiménez
Ana I
AI
Cativiela
Carlos
C