title: Towards the stereoselective synthesis of alpha-methylated (2S,3aS,7aS)-octahydroindole-2-carboxylic acid.
abstract: 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.
authors.affiliation: Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragón, Universidad de Zaragoza-CSIC, 50009 Zaragoza, Spain.
authors.forename: Francisco J
authors.initials: FJ
authors.lastname: Sayago
authors.forename: M Isabel
authors.initials: MI
authors.lastname: Calaza
authors.forename: Ana I
authors.initials: AI
authors.lastname: Jiménez
authors.forename: Carlos
authors.initials: C
authors.lastname: Cativiela