Catalytic Dynamic Resolution Applied to the Synthesis of 2,6-Disubstituted Piperidines: Preparation of (+)-Lupetidine and (-)-Epidihydropinidine

by Beng, Timothy Kum; Gawley, Robert E.

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. double dagger Dedicated to Professor Al Padwa, on the occasion of his 75th birthday, in admiration of his many contributions to heterocyclic chemistry, and in envy of his vigor in climbing mountains of both the chemical and geologic variety.

Journal
Heterocycles
Volume
84
Issue
2
Year
2012
Start Page
697
ISBN/ISSN
1881-0942; 0385-5414
DOI
10.3987/COM-11-S(P)45