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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. © 2002 The Royal Society of Chemistry.

Original publication

DOI

10.1039/b205326h

Type

Journal article

Journal

Journal of the Chemical Society. Perkin Transactions 1

Publication Date

31/05/2002

Volume

2

Pages

1869 - 1876