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Enantioselective Synthesis of α-Amino Nitriles from <i>N</i>-Benzhydryl Imines and HCN with a Chiral Bicyclic Guanidine as Catalyst

Organic Letters · 1999 · Vol. 1(1) · pp. 157–160

E. J. Corey✉(Harvard University)Michael J. Grogan(Harvard University)

Abstract

A novel catalytic enantioselective Strecker synthesis of chiral α-amino nitriles and α-amino acids is described and analyzed with regard to the possible mechanistic basis for stereoselectivity. Key features of the enantioselective process include (1) the use of the chiral bicyclic guanidine 1 as catalyst and (2) the use of the N-benzhydryl substituent on the imine substrate.

Asymmetric Synthesis and Catalysis Synthesis and Catalytic Reactions Advanced Synthetic Organic ChemistryEnantioselective synthesisChemistryImineBicyclic moleculeCatalysisSubstituentStereoselectivityGuanidineStereochemistryOrganic chemistry

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