Date of Award

1-1-2013

Document Type

Open Access Dissertation

Department

Chemistry and Biochemistry

Sub-Department

Organic chemistry

First Advisor

Sheryl L Wiskur

Abstract

The thesis describes the silylation-based kinetic resolution for α-hydroxy carbonyl compounds catalyzed by isothiourea catalyst as well as our effort to make novel chiral isothiourea catalyst.

In Chapter 1, general background will be introduced, including chirality, general methods to obtain enantiopure compounds and kinetic resolution. In Chapter 2, the mechanism of the chiral recognition was discussed and a novel isothiourea catalyst was design to investigate the mechanism. The synthesis of the new catalyst was also described in this chapter.

In Chapter 3, the silylation-based kinetic resolution for α-hydroxy carbonyl compounds will be discussed. Since silylation-based kinetic resolution have already been proven very effective to make enantiopure monofunctional secondary alcohol, it is interesting to investigate the application of this methodology to α-hydroxy carbonyl compounds, which have similar core structure with monofunctional secondary alcohol for the chiral recognition. The optimized reaction conditions have already established and the substrate-scope have already been studied.

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