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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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Publication details

The article was received on 31 May 2002, accepted on 03 Jul 2002 and first published on 18 Jul 2002


Article type: Paper
DOI: 10.1039/B205326H
Citation: J. Chem. Soc., Perkin Trans. 1, 2002, 1869-1876
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    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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