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Issue 16, 2002
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N-Acyl ‘Quat’ pyrrolidinone auxiliary as a chiral amide equivalent via direct aminolysis

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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

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Article information


Submitted
31 May 2002
Accepted
03 Jul 2002
First published
18 Jul 2002

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

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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