Access to 2,6-disubstituted piperidines: control of the diastereoselectivity, scope, and limitations. Applications to the stereoselective synthesis of (-)-solenopsine A and alkaloid (+)-241D

Abstract

Scope and limitations in the diastereoselective preparation of 2,6-cis or 2,6-trans disubstituted piperidines are described, through intramolecular reaction of chiral β'-carbamate-α,β-unsaturated ketone. This methodology has been applied to the total synthesis of a few well chosen examples, such as (-)-solenopsine A and alkaloid (+)-241D.