Organic letters

Synthesis of trans-(3 S)-Amino-(4 R)-alkyl-and-(4 S)-Aryl-piperidines via Ring-Closing Metathesis Reaction

XE Hu, NK Kim, B Ledoussal

Index: Hu, X. Eric; Kim, Nick K.; Ledoussal, Benoit Organic Letters, 2002 , vol. 4, # 25 p. 4499 - 4502

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Citation Number: 29

Abstract

trans-(3 S)-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 trans-(3 S)-amino-(4 R)-alkyl-and-(4 S)-aryl-piperidines. This procedure presents the first method for the asymmetric synthesis of 4-substituted 3-amino ...

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