Enantioselective Cyanosilylation of Ketones with Lithium(I) Dicyanotrimethylsilicate(IV) Catalyzed by a Chiral Lithium(I) Phosphoryl Phenoxide | Zendy

Hatano Manabu | Zendy; Yamakawa Katsuya | Zendy; Kawai Tomoaki | Zendy; Horibe Takahiro | Zendy; Ishihara Kazuaki | Zendy

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Enantioselective Cyanosilylation of Ketones with Lithium(I) Dicyanotrimethylsilicate(IV) Catalyzed by a Chiral Lithium(I) Phosphoryl Phenoxide

Author(s) -

Hatano Manabu,

Yamakawa Katsuya,

Kawai Tomoaki,

Horibe Takahiro,

Ishihara Kazuaki

Publication year - 2016

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.201510682

Subject(s) - enantioselective synthesis , lithium (medication) , reagent , catalysis , chemistry , organic chemistry , combinatorial chemistry , medicine , endocrinology

A highly enantioselective cyanosilylation of ketones was developed by using a chiral lithium(I) phosphoryl phenoxide aqua complex as an acid/base cooperative catalyst. The pentacoordinate silicate generated in situ from Me 3 SiCN/LiCN acts as an extremely reactive cyano reagent. Described is a 30 gram scale reaction and the synthesis of the key precursor to (+)‐13‐hydroxyisocyclocelabenzine.

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