Journal
ORGANIC LETTERS
Volume 4, Issue 22, Pages 3781-3784Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol026315w
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- NIGMS NIH HHS [GM59945] Funding Source: Medline
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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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