The First Catalytic Asymmetric Addition of Dialkylzincs to α-Ketoesters

Autor: DiMauro, E. F., Kozlowski, M. C.
Zdroj: Organic Letters; October 2002, Vol. 4 Issue: 22 p3781-3784, 4p
Abstrakt: The first catalytic, enantioselective addition of organozinc reagents to α-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. α-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 α-hydroxy acid.
Databáze: Supplemental Index