Literature DB >> 20011581

Towards the stereoselective synthesis of alpha-methylated (2S,3aS,7aS)-octahydroindole-2-carboxylic acid.

Francisco J Sayago1, M Isabel Calaza, Ana I Jiménez, Carlos Cativiela.   

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.

Entities:  

Year:  2008        PMID: 20011581      PMCID: PMC2711560          DOI: 10.1016/j.tetasy.2008.11.030

Source DB:  PubMed          Journal:  Tetrahedron Asymmetry        ISSN: 0957-4166


  16 in total

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  1 in total

1.  A straightforward route to enantiopure alpha-substituted derivatives of (2S,3aS,7aS)-octahydroindole-2-carboxylic acid.

Authors:  Francisco J Sayago; M Isabel Calaza; Ana I Jiménez; Carlos Cativiela
Journal:  Tetrahedron       Date:  2009-07-01       Impact factor: 2.457

  1 in total

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