ORCID Identifier(s)

0000-0001-5174-8586

Graduation Semester and Year

2021

Language

English

Document Type

Thesis

Degree Name

Master of Science in Chemistry

Department

Chemistry and Biochemistry

First Advisor

Junha Jeon

Abstract

This research focuses on the design and synthesis of enantioselective desymmetrizing α-hydrosilylation of propargyl alcohols to provide α-hydroxy (E)-vinylsilanes. Transition metal-catalyzed, regio-and stereoselective intramolecular hydrosilylation of propargylic alcohols with an easily removable acetal directing group has been studied. This project thus far screened 35 chiral ligands with rhodium (I) to achieve enantioselective alkyne hydrosilylation. This strategy consists of sequential hydrosilylation of bis-propargyl formate with iridium catalyst and intramolecular alkyne hydrosilylation with chiral rhodium catalyst. To this end, a variety of chiral phosphine ligands has been tested, yet an enantiomeric excess of the α-hydroxy (E)-vinylsilanes has not been fruitful thus far, which was determined by chiral HPLC analysis. However, the result showed that the bulkier chiral ligands generally gave better enantioselectivity. In future, further ligand screening as well as structural modification of hydrosilane will be performed to achieve the enantioselective intramolecular α-hydrosilylation of propargyl alcohols.

Keywords

Hydrosilylation

Disciplines

Chemistry | Physical Sciences and Mathematics

Comments

Degree granted by The University of Texas at Arlington

Included in

Chemistry Commons

Share

COinS