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^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University
Nankai University

Research output: Contribution to journal › Article › peer-review

72 Scopus citations

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.

Original language	English
Pages (from-to)	8730-8733
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	138
Issue number	28
DOIs	https://doi.org/10.1021/jacs.6b05601
State	Published - 20 Jul 2016

Access to Document

10.1021/jacs.6b05601

Cite this

@article{e7cc80bad9b6470cad7d98689a8da0f8,

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

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",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

month = jul,

day = "20",

doi = "10.1021/jacs.6b05601",

language = "英语",

volume = "138",

pages = "8730--8733",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "28",

}

TY - JOUR

T1 - Me2(CH2Cl)SiCN

T2 - Bifunctional Cyanating Reagent for the Synthesis of Tertiary Alcohols with a Chloromethyl Ketone Moiety via Ketone Cyanosilylation

AU - Zeng, Xing Ping

AU - Zhou, Jian

PY - 2016/7/20

Y1 - 2016/7/20

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.

UR - https://www.scopus.com/pages/publications/84979277048

U2 - 10.1021/jacs.6b05601

DO - 10.1021/jacs.6b05601

M3 - 文章

AN - SCOPUS:84979277048

SN - 0002-7863

VL - 138

SP - 8730

EP - 8733

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 28

ER -

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

Abstract

Access to Document

Other files and links

Fingerprint

Cite this