Access to 2,6-Disubstituted Piperidines: Control of the Diastereoselectivity, Scope, and Limitations. Applications to the Stereoselective Synthesis of (−)-Solenopsine A and Alkaloid (+)-241D

• DOI: 10.1021/jo302712f
• Publication Date: 2013-02-12T03:02:50Z
• Authors: Isabelle Abrunhos...; Aurélie Plas; Alexandre Vogrig; Nishanth Kandepedu; Pierre Chalard; Yves Troin
• Keywords: Scope (computer science); Carbamate

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