The Journal of Organic Chemistry

Acyclic stereoselection. 8. A new class of reagents for the highly stereoselective preparation of threo-2-alkyl-3-hydroxycarboxylic acids by the aldol condensation

MC Pirrung, CH Heathcock

Index: Pirrung, Michael C.; Heathcock, Clayton H. Journal of Organic Chemistry, 1980 , vol. 45, # 9 p. 1727 - 1728

Full Text: HTML

Citation Number: 70

Abstract

Summary: threo-3-Hydroxy-2-methylcarboxylic acids may be prepared in high stereochemical yield by condensing aryl propionates 1 or 2 with aldehydes followed by hydrolytic or oxidative removal of the aryl group. Sir: The recent flurry of activity on stereoselective aldol condensations has resulted in methods for realizing high stereochemical control (> 95%) in the preparation of er-