Issue 16, 2002

N-Acyl ‘Quat’ pyrrolidinone auxiliary as a chiral amide equivalent via direct aminolysis

Abstract

A novel route to chiral amides through the efficient, non-racemising, cleavage of N-acyl side chains from a ‘Quat’ chiral auxiliary using N-centred nucleophiles is described. The synthetic utility of the procedure is then highlighted by the preparation of a range of succinamide and succinimide derivatives and through the synthesis of the natural product (S)-(+)-amphetamine via a stereospecific Hofman type degradation using a hypervalent iodine reagent.

Graphical abstract: N-Acyl ‘Quat’ pyrrolidinone auxiliary as a chiral amide equivalent via direct aminolysis

Article information

Article type
Paper
Submitted
31 May 2002
Accepted
03 Jul 2002
First published
18 Jul 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 1869-1876

N-Acyl ‘Quat’ pyrrolidinone auxiliary as a chiral amide equivalent via direct aminolysis

S. G. Davies and D. J. Dixon, J. Chem. Soc., Perkin Trans. 1, 2002, 1869 DOI: 10.1039/B205326H

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