Issue 69, 2014

Synthesis and kinetic resolution of N-Boc-2-arylpiperidines

Abstract

The chiral base n-BuLi/(−)-sparteine or n-BuLi/(+)-sparteine surrogate promotes kinetic resolution of N-Boc-2-arylpiperidines by asymmetric deprotonation. The enantioenriched starting material was recovered with yields 39–48% and ers up to 97 : 3. On lithiation then electrophilic quench, 2,2-disubstituted piperidines were obtained with excellent yields and enantioselectivities.

Graphical abstract: Synthesis and kinetic resolution of N-Boc-2-arylpiperidines

Supplementary files

Article information

Article type
Communication
Submitted
16 Jun 2014
Accepted
11 Jul 2014
First published
11 Jul 2014
This article is Open Access
Creative Commons BY license

Chem. Commun., 2014,50, 9910-9913

Synthesis and kinetic resolution of N-Boc-2-arylpiperidines

E. J. Cochrane, D. Leonori, L. A. Hassall and I. Coldham, Chem. Commun., 2014, 50, 9910 DOI: 10.1039/C4CC04576A

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