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

Chemical Communications Pub Date: 2014-07-11 DOI: 10.1039/C4CC04576A

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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