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Paper | Special issue | Vol 84, No. 2, 2012, pp.697-718
Published online, 17th August, 2011
DOI: 10.3987/COM-11-S(P)45
Catalytic Dynamic Resolution Applied to the Synthesis of 2,6-Disubstituted Piperidines: Preparation of (+)-Lupetidine and (–)-Epidihydropinidine

Timothy K. Beng and Robert E. Gawley*

*Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, Arkansas 72701, U.S.A.

Abstract

The diastereoselective synthesis of trans-2,6-disubstituted piperidines has been rendered enantioselective by incorporating a catalytic dynamic resolution into the first alkylation step. The method has been applied to the synthesis of (–)-epidihydropinidine and (+)-trans-lupetidine.