Title

Cyclization of achiral organolithiums controlled by a stereogenic lithium

Date of Completion

January 2004

Keywords

Chemistry, Organic

Degree

Ph.D.

Abstract

The cyclization of substituted 5-hexenyllithiums has been examined. Various carbocycles and heterocycles have been prepared via anionic cyclization of unsaturated achiral olefinic organolithiums. These cyclizations have been found to proceed in an enantiofacially selective fashion when conducted in the presence of enantiopure, nonracemic chiral ligands. This methodology has been applied to the preparation of enantioenriched indolines and pyrrolidines, as well as to the total syntheses of the sesquiterpenes, (R)cuparene and (R)-herbertene. ^