Multicenter Strategy for the Development of Catalytic Enantioselective Nucleophilic Alkylation of Ketones: Me 2 Zn Addition to α‐Ketoesters | Zendy

Funabashi Ken | Zendy; Jachmann Markus | Zendy; Kanai Motomu | Zendy; Shibasaki Masakatsu | Zendy

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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).

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