The Diastereoselective Barbier-Type Addition to Chiral N-Tosylimines

Abstract

The Barbier approach was used for diastereoselective formation of allylamino acid derivatives. The stereochemical models for nucleophilic addition to N-tosylimines bearing various chiral auxiliaries such as (2R)-bornano-10,2-sultam, (R)-8-phenylmenthol, and 10-N,N-dicyclohexylsulfamoyl-(R)-isoborneol are proposed.

Key words

chiral auxiliaries - imines - nucleophilic additions - organometallic reagents - stereoselectivity

References

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The crystallographic data for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-194392. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK [fax [phone]; e-mail: [e-mail]].