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Atropisomeric amides: stereoselective enolate chemistry and enantioselective synthesis via a new SmI2-mediated reduction

Journal of the Chemical Society Perkin Transactions 1Published 1 January 1999
Adam D. Hughes, David A. Price, Nigel S. Simpkins
Citations87

TL;DR

The use of certain types of atropisomeric amides, incorporating an N-MEM-ortho-tert-butylaniline group, for stereoselective reactions, has been explored.

Abstract

The use of certain types of atropisomeric amides, incorporating an N-MEM-ortho-tert-butylaniline group, for stereoselective reactions, has been explored. Enolate reactions of these systems are highly diastereocontrolled, and enantiomerically enriched starting materials can be obtained, starting from lactic acid, via a new SmI2 mediated reduction process.

Keywords

Chemistry