Date of Graduation

12-2011

Document Type

Dissertation

Degree Name

Doctor of Philosophy in Chemistry (PhD)

Degree Level

Graduate

Department

Chemistry & Biochemistry

Advisor

Robert E. Gawley

Committee Member

Mattias McIntosh

Second Committee Member

James Hinton

Third Committee Member

Neil Allison

Keywords

Pure sciences; Asymmetric catalysis; Copper carbenoid; Enantioselective hydrosilylation; Heterocyclic carbenes

Abstract

A copper carbenoid representative of a novel class of N-heterocyclic carbene (NHC) catalysts has been synthesized. This compound was characterized by X-ray crystallography and was found to confirm the rationale of our synthetic design: The C2-symmetric structure places four stereocenters in close proximity (<5Å) to the reactive site of the carbene via a trans-annular gearing effect. The copper carbenoid was found to catalyze the hydrosilylation of prochiral ketones with superb selectivity in high yield.

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