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Issue 69, 2014
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Synthesis and kinetic resolution of N-Boc-2-arylpiperidines

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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

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Supplementary files

Article information


Submitted
16 Jun 2014
Accepted
11 Jul 2014
First published
11 Jul 2014

This article is Open Access

Chem. Commun., 2014,50, 9910-9913
Article type
Communication

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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