Issue 39, 2013

Enantioselective synthesis of 2-substituted and 3-substituted piperidines through a bromoaminocyclization process

Abstract

A catalytic enantioselective bromocyclization of olefinic amides using amino-thiocarbamates as the catalysts has been developed. The resulting enantioenriched 2-substituted 3-bromopiperidines can readily be transformed to 3-substituted piperidines through a silver salt-mediated rearrangement. This process has been applied to the synthesis of a dopaminergic drug, Preclamol.

Graphical abstract: Enantioselective synthesis of 2-substituted and 3-substituted piperidines through a bromoaminocyclization process

Supplementary files

Article information

Article type
Communication
Submitted
10 Sep 2012
Accepted
02 Oct 2012
First published
03 Oct 2012

Chem. Commun., 2013,49, 4412-4414

Enantioselective synthesis of 2-substituted and 3-substituted piperidines through a bromoaminocyclization process

L. Zhou, D. W. Tay, J. Chen, G. Y. C. Leung and Y. Yeung, Chem. Commun., 2013, 49, 4412 DOI: 10.1039/C2CC36578B

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