Alkylation of phenylglycinol-derived bicyclic lactams. Enantioselective synthesis of 3-alkylpiperidines

Abstract

The stereochemical outcome of the alkylation of simple phenylglycinol- derived bicyclic lactams has been studied. The method provides a simple and concise route to 3-alkylpiperidines in both enantiomeric series. The synthesis of (+)-R-decarbomethoxytetrahydrosecodine, an indole alkaloid embodying a 3-ethylpiperidine moiety, is reported. ©ARKAT.