Aldol condensation of Evans chiral enolates with acetophenones. Its application to the stereoselective synthesis of homochiral antifungal agents

J Bartroli, E Turmo, J Belloc, J Forn

Index: Bartroli; Turmo; Belloc; Forn Journal of Organic Chemistry, 1995 , vol. 60, # 10 p. 3000 - 3012

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Citation Number: 38

Abstract

The results of the aldol condensation of Evans chiral imide enolates with a series of acetophenones are reported. Activated acetophenones, such as 2, 4-difluoroacetophenone, a-chloroacetophenone, and a-chloro-and a-bromo-2, 4-difluoroacetophenone, reacted with the lithium enolate of 5 with good levels of enolate facial diastereoselectivity toward the (2R)- isomers (> 1O: l) but with low anti: syn selectivity (ca. 3: 2). Sodium and potassium ...