The Synthesis of Chiral Functionalised Piperidines Using a Reverse-Cope Cyclisation: The Effect of Solvent on Diastereoselectivity

Ian A. O'Neil; Ed Cleator; J. Mike Southern; Neal Hone; David J. Tapolczay

doi:10.1055/s-2000-6624

Synlett 2000; 2000(5): 0695-0697
DOI: 10.1055/s-2000-6624

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The Synthesis of Chiral Functionalised Piperidines Using a Reverse-Cope Cyclisation: The Effect of Solvent on Diastereoselectivity

Ian A. O'Neil^* , Ed Cleator, J. Mike Southern, Neal Hone, David J. Tapolczay

^*Department of Chemistry, University of Liverpool, Crown St, Liverpool L69 7ZD, UK

Abstract

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Ring opening of a chiral epoxide with N-benzylhydroxylamine in methanol followed by an in situ reverse-Cope cyclisation in a variety of solvents gives the N-benzylpiperidine N-oxide as mixtures of diastereoisomers. Ring opening and cyclisation can be carried out in a one pot sequence to give up to a 5:1 mixture of diastereoisomers. The role of the solvent on the diastereoselectivity of the reaction is examined.

piperidines - asymmetric synthesis - cyclisation - hydroxylamine

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