Title

Investigation of the asymmetric Doering-Moore-Skattebol synthesis of allenes and carbolithiation methodologies

Date of Completion

January 2010

Keywords

Chemistry, Organic

Degree

Ph.D.

Abstract

The asymmetric Doering-Moore-Skattebøl synthesis of allenes has been investigated. A modest enantioselectivity was observed in the presence of (−)-sparteine as a chiral ligand. Kinetic resolution of racemic 1,2-cyclononadiene was observed under certain conditions. An intramolecular carbolithiation route to all isomeric azaindolines was developed by the cyclization of aryllithiums derived from (N,N-diallylamino)bromopyridines. ^