Physical Sciences and Mathematics Commons^™

A Silylation Based Kinetic Resolution Of Secondary Alcohols And The Synthesis And Structural Characterization Of Pyridyl-Oxazolidine Compounds, Cody Ian Sheppard

Theses and Dissertations

Described herein is the first enantioselective silylation based kinetic resolution of monofunctional secondary alcohols to achieve useful levels of enantioselectivity. Using commercially available reagents, the reaction conditions were optimized and found to successfully resolve several secondary alcohols with high enantioselectivity. It was discovered that the nucleophilic isothiourea compound (-)-tetramisole, with Ph3SiCl as the silyl source, gave superior results to other nucleophilic catalysts and was capable of performing the kinetic resolution in as little as 45 minutes using mild reaction conditions. The structural and electronic characteristics of successful and less successful substrates are also discussed.

Chapter three discusses mechanistic investigations and …