手性膦氧锂催化的手性锂双氰胺基三甲硅基硅烷对酮的对映选择性氰硅烷化反应
Enantioselective Cyanosilylation of Ketones with Lithium(I) Dicyanotrimethylsilicate(IV) Catalyzed by a Chiral Lithium(I) Phosphoryl Phenoxide.
机构信息
Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya, 464-8603, Japan.
Japan Science and Technology Agency (JST), CREST, Furo-cho, Chikusa, Nagoya, 464-8603, Japan.
出版信息
Angew Chem Int Ed Engl. 2016 Mar 14;55(12):4021-5. doi: 10.1002/anie.201510682. Epub 2016 Feb 2.
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 Me3SiCN/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.
发展了一种手性锂（I）膦氧酚盐水合配合物作为酸/碱协同催化剂，实现酮的高对映选择性氰硅烷化反应。Me3SiCN/LiCN 原位生成的五配位硅酸盐作为一种极其活泼的氰基试剂。描述了 30 克规模的反应以及（+）-13-羟基异环海罂粟碱关键前体的合成。
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