Issue 33, 2014

Asymmetric synthesis of substituted NH-piperidines from chiral amines

Abstract

Previously, we reported an efficient asymmetric synthesis of substituted piperidines through an exocyclic chirality induced nitroalkene/amine/enone (NAE) condensation reaction. An effective protecting group strategy was developed herein to achieve enantiopure piperidines (yields up to 92%) with complete chirality retention (ee > 95%). A simple derivatization of the obtained piperidines gave thiourea catalysts, indicating the strong potential of this method for producing new amine-based dual functional organocatalysts for future development.

Graphical abstract: Asymmetric synthesis of substituted NH-piperidines from chiral amines

Supplementary files

Article information

Article type
Paper
Submitted
27 Mar 2014
Accepted
14 May 2014
First published
15 May 2014

Org. Biomol. Chem., 2014,12, 6384-6388

Author version available

Asymmetric synthesis of substituted NH-piperidines from chiral amines

L. N. Gautam, Y. Su, N. G. Akhmedov, J. L. Petersen and X. Shi, Org. Biomol. Chem., 2014, 12, 6384 DOI: 10.1039/C4OB00657G

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