Asymmetric synthesis of trans-2,6-disubstituted piperidines from sulfinimine-derived d-amino b-ketophosphonates. Total synthesis of (-)-myrtine

ORGN 123

Franklin A Davis, He Xu, and Junyi Zhang. Department of Chemistry, Temple University, Philadelphia, PA 19122
N-Sulfinyl d-amino b-ketophosphonates, readily prepared from enantiopure sulfinimines, are transformed to dihydropyridones, which are subject to Michael addition and dephosphonylation to afford trans-2,6-disubstituted piperidines. The total synthesis of (-)-myrtine is described.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006