Journal
ORGANIC LETTERS
Volume 4, Issue 25, Pages 4499-4502Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol027019m
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[GRAPHICS] trans-(3S)-Amino piperidines bearing various alkyl and aryl substituents at the C-4 position were synthesized via a ring-closing metathesis reaction. The absolute stereochemistry was controlled using a protected D-serine as a starting material. Stereoselective hydrogenation of allylamines provided transn-(3S)-amino-(4R)-alkyl- and -(4S)-aryl-piperidines. This procedure presents the first method for the asymmetric synthesis of 4-substituted 3-amino piperidines.
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