The first catalytic asymmetric addition of dialkylzincs to α-ketoesters

被引：86
作者：
DiMauro, EF [1 ]
Kozlowski, MC [1 ]
机构：
[1] Univ Penn, Roy & Diana Vagelos Labs, Dept Chem, Philadelphia, PA 19104 USA
来源：
ORGANIC LETTERS | 2002年 / 4卷 / 22期
关键词：
D O I：
10.1021/ol026315w
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
graphic The first catalytic, enantioselective addition of organozinc reagents to alpha-ketoesters is described. Modular bifunctional salen catalysts that contain Lewis acid and Lewis base activating groups accelerate the carbonyl addition to a much greater extent than the competing carbonyl reduction. alpha-Hydroxyesters containing new quaternary stereogenic centers are obtained in high yield and moderate enantiomeric excess. Enrichment to 98% ee can be effected by recrystallization of the corresponding alpha-hydroxy acid.
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页码：3781 / 3784
页数：4
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