Me2(CH2Cl)SiCN: Bifunctional Cyanating Reagent for the Synthesis of Tertiary Alcohols with a Chloromethyl Ketone Moiety via Ketone Cyanosilylation

Xing Ping Zeng; Jian Zhou

doi:10.1021/jacs.6b05601

Me₂(CH₂Cl)SiCN: Bifunctional Cyanating Reagent for the Synthesis of Tertiary Alcohols with a Chloromethyl Ketone Moiety via Ketone Cyanosilylation

Xing Ping Zeng
, Jian Zhou^*

^*此作品的通讯作者

化学与分子工程学院

East China Normal University
Nankai University

科研成果: 期刊稿件 › 文章 › 同行评审

72 引用（Scopus）

摘要

We report a novel bifunctional cyanating reagent, Me₂(CH₂Cl)SiCN, which paves the way to a one-pot sequential synthesis of tertiary alcohols featuring a chloromethyl ketone moiety via enantioselective ketone cyanosilylation. This method contributes to gram-scale enantioselective total synthesis of the aggregation pheromone of the Colorado potato beetle, (S)-CPB.

源语言	英语
页（从-至）	8730-8733
页数	4
期刊	Journal of the American Chemical Society
卷	138
期	28
DOI	https://doi.org/10.1021/jacs.6b05601
出版状态	已出版 - 20 7月 2016

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10.1021/jacs.6b05601

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abstract = "We report a novel bifunctional cyanating reagent, Me2(CH2Cl)SiCN, which paves the way to a one-pot sequential synthesis of tertiary alcohols featuring a chloromethyl ketone moiety via enantioselective ketone cyanosilylation. This method contributes to gram-scale enantioselective total synthesis of the aggregation pheromone of the Colorado potato beetle, (S)-CPB.",

author = "Zeng, \{Xing Ping\} and Jian Zhou",

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AU - Zhou, Jian

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N2 - We report a novel bifunctional cyanating reagent, Me2(CH2Cl)SiCN, which paves the way to a one-pot sequential synthesis of tertiary alcohols featuring a chloromethyl ketone moiety via enantioselective ketone cyanosilylation. This method contributes to gram-scale enantioselective total synthesis of the aggregation pheromone of the Colorado potato beetle, (S)-CPB.

AB - We report a novel bifunctional cyanating reagent, Me2(CH2Cl)SiCN, which paves the way to a one-pot sequential synthesis of tertiary alcohols featuring a chloromethyl ketone moiety via enantioselective ketone cyanosilylation. This method contributes to gram-scale enantioselective total synthesis of the aggregation pheromone of the Colorado potato beetle, (S)-CPB.

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Me2(CH2Cl)SiCN: Bifunctional Cyanating Reagent for the Synthesis of Tertiary Alcohols with a Chloromethyl Ketone Moiety via Ketone Cyanosilylation

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Me₂(CH₂Cl)SiCN: Bifunctional Cyanating Reagent for the Synthesis of Tertiary Alcohols with a Chloromethyl Ketone Moiety via Ketone Cyanosilylation