Approaches to Asymmetric Synthesis. The Diastereoselective Alkylations of Chiral Propionamide Enolates

Author: Takacs, James Michael

Year: 1981

Degree: Dissertation (Ph.D.)

Advisor: Dervan, Peter B.

Committee Members: Dervan, Peter B.; Evans, David A.; Ireland, Robert E.; Richards, John H.

Option: Chemistry

DOI: 10.7907/f2kf-9406

Abstract

Enantioselective propionate alkylation, as a method to control acyclic methyl~bearing stereocenters, is achieved via the diastereoselective alkylation of chiral propionamide enolates. The factors which control stereoselective enolization, diastereotopic differentiation of the enolate system, and selective cleavage of the chiral auxiliary are discussed. The application to the preparation of simple chiral carboxylic acids proceeds with the highest optical yields yet reported.

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