Premium
Multicenter Strategy for the Development of Catalytic Enantioselective Nucleophilic Alkylation of Ketones: Me 2 Zn Addition to α‐Ketoesters
Author(s) -
Funabashi Ken,
Jachmann Markus,
Kanai Motomu,
Shibasaki Masakatsu
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200351650
Subject(s) - enantioselective synthesis , catalysis , heteroatom , alkylation , chemistry , nucleophilic addition , nucleophile , zinc , organic chemistry , combinatorial chemistry , ring (chemistry)
An array of heteroatoms is essential for the activity and enantioselectivity of the catalyst 2 in the addition of Me 2 Zn to α‐ketoesters 1 (e.g. see equation). α‐Hydroxyesters 3 were obtained with up to 96 % ee in the presence of a catalytic amount of additive i PrOH, which serves to generate the catalytically active monomeric species (based on the observation of nonlinear effects).