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

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 cat...

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Bibliographic Details
Published in:Organic letters 1999-07, Vol.1 (1), p.157-160
Main Authors: Corey, E. J, Grogan, Michael J
Format: Article
Language:English
Subjects:
Benzhydryl Compounds - chemical synthesis
Bridged Bicyclo Compounds - chemistry
Catalysis
Guanidines - chemistry
Hydrogen Cyanide - chemistry
Imines - chemical synthesis
Models, Molecular
Nitriles - chemical synthesis
Schiff Bases
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol990623l