Part I. Development of an enantioselective cyclopropanation reagent. Part II. Studies on the addition of organometallic reagents to imine derivatives

Efforts to develop an enantioselective zinc-based cyclopropanation reagent are described. Enantioselectivities of up to 24% e.e. were achieved using N-methylephedrine as a chiral controller ligand for iodomethylzinc cyclopropanations of cinnamyl alcohol. Chiral bis-ether complexes of bis(iodomethyl)zinc were found to react sluggishly and without enantiocontrol, indicating that the use of chelating ligands dramatically attenuates the reactivity of iodomethylzinc species.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2011

Author dc:creator

• Edwards, James Patrick

Contributors dc:contributor

• Denmark, Scott E.

• Chemistry, Organic

Statement dc:rights

• Copyright 1991 Edwards, James Patrick

Language dc:language

eng

Identifier

AAI9210792
(UMI)AAI9210792

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/19631