Date of Graduation

8-2016

Document Type

Dissertation

Degree Name

Doctor of Philosophy in Chemistry (PhD)

Degree Level

Graduate

Department

Chemistry & Biochemistry

Advisor

Matt Mcintosh

Committee Member

Neil Allison

Second Committee Member

Bill Durham

Third Committee Member

Feng Wang

Keywords

Pure Sciences; Assymetic synthetic

Abstract

CuIPhEt is a C2-symmetric N-heterocyclic carbene catalyst used in the asymmetric hydrosilylation of a variety of prochiral ketones with good yields and selectivities. The large-scale, five-step synthesis of this carbene has been devised. The second step of the synthetic plan includes a double asymmetric hydrogenation of a 1,1-diaryl alkene—a traditionally difficult transformation. The procedure for the use of CuIPhEt in asymmetric hydrosilylations has been optimized and used on both the originally published substrate scope and new compounds. This protocol for the hydrosilylation has been applied in a 10 g reduction to create an intermediate for use toward the total synthesis of antascomicin B. A class of 2-ketoazoles was synthesized for use in asymmetric hydrosilylations, but only poor selectivities were observed.

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