Title

Highly Enantioselective Organocatalysis of Michael Addition of Oxyaldehydes to Nitroolefins

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

Date of Award

Fall 2013

Abstract

A novel category of diarylprolinol silyl ether catalyst, which when used in conjunction with an acidic co-catalyst, generates an ammonium salt supported recyclable organocatalyst. This catalytic system is shown to be very effective for the Michael reaction of various oxyaldehydes and nitroolefins in isopropanol. Excellent enantioselectivies (up to 99%) and diastereoselectivities (syn/anti of 75:25) were obtained. Compared to other catalysts used for these model reactions, excellent enantioselectivites were obtained in shorter reaction times in water miscible solvents.

Advisor

Allan Headley

Subject Categories

Chemistry | Physical Sciences and Mathematics

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