A general and efficient Lewis acid catalysed Mukaiyama-aldol reaction of difluoroenoxysilanes and ketones

Fu Min Liao; Xiao Tong Gao; Xiao Si Hu; Shi Liang Xie; Jian Zhou

doi:10.1016/j.scib.2017.10.016

A general and efficient Lewis acid catalysed Mukaiyama-aldol reaction of difluoroenoxysilanes and ketones

Fu Min Liao
, Xiao Tong Gao
, Xiao Si Hu
, Shi Liang Xie
, 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

26 引用（Scopus）

摘要

We report a general and highly efficient Mukaiyama-aldol reaction of ketones and difluoroenoxysilanes. While the reaction of aryl ketones worked efficiently in the presence of Bi(OTf)₃, that of aliphatic ketones required the use of Sc(OTf)₃. In addition, Sc(OTf)₃ was capable of achieving excellent 1,2-selectivity in the corresponding reaction of α,β-unsaturated ketones. This method provides a facile access to differently substituted β-hydroxy α,α-difluoro ketones, versatile synthons for difluomethylated tertiary alcohols.

源语言	英语
页（从-至）	1504-1509
页数	6
期刊	Science Bulletin
卷	62
期	22
DOI	https://doi.org/10.1016/j.scib.2017.10.016
出版状态	已出版 - 30 11月 2017

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10.1016/j.scib.2017.10.016

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@article{0cf74a1847464586b89fce9b1bbe5bb3,

title = "A general and efficient Lewis acid catalysed Mukaiyama-aldol reaction of difluoroenoxysilanes and ketones",

abstract = "We report a general and highly efficient Mukaiyama-aldol reaction of ketones and difluoroenoxysilanes. While the reaction of aryl ketones worked efficiently in the presence of Bi(OTf)3, that of aliphatic ketones required the use of Sc(OTf)3. In addition, Sc(OTf)3 was capable of achieving excellent 1,2-selectivity in the corresponding reaction of α,β-unsaturated ketones. This method provides a facile access to differently substituted β-hydroxy α,α-difluoro ketones, versatile synthons for difluomethylated tertiary alcohols.",

keywords = "Difluoroenoxysilanes, Ketones, Lewis acid catalysed, Mukaiyama-aldol reaction, β-Hydroxy α,α-difluoro ketones",

author = "Liao, \{Fu Min\} and Gao, \{Xiao Tong\} and Hu, \{Xiao Si\} and Xie, \{Shi Liang\} and Jian Zhou",

note = "Publisher Copyright: {\textcopyright} 2017 Science China Press",

year = "2017",

month = nov,

day = "30",

doi = "10.1016/j.scib.2017.10.016",

language = "英语",

volume = "62",

pages = "1504--1509",

journal = "Science Bulletin",

issn = "2095-9273",

publisher = "Elsevier B.V.",

number = "22",

}

TY - JOUR

T1 - A general and efficient Lewis acid catalysed Mukaiyama-aldol reaction of difluoroenoxysilanes and ketones

AU - Liao, Fu Min

AU - Gao, Xiao Tong

AU - Hu, Xiao Si

AU - Xie, Shi Liang

AU - Zhou, Jian

PY - 2017/11/30

Y1 - 2017/11/30

N2 - We report a general and highly efficient Mukaiyama-aldol reaction of ketones and difluoroenoxysilanes. While the reaction of aryl ketones worked efficiently in the presence of Bi(OTf)3, that of aliphatic ketones required the use of Sc(OTf)3. In addition, Sc(OTf)3 was capable of achieving excellent 1,2-selectivity in the corresponding reaction of α,β-unsaturated ketones. This method provides a facile access to differently substituted β-hydroxy α,α-difluoro ketones, versatile synthons for difluomethylated tertiary alcohols.

AB - We report a general and highly efficient Mukaiyama-aldol reaction of ketones and difluoroenoxysilanes. While the reaction of aryl ketones worked efficiently in the presence of Bi(OTf)3, that of aliphatic ketones required the use of Sc(OTf)3. In addition, Sc(OTf)3 was capable of achieving excellent 1,2-selectivity in the corresponding reaction of α,β-unsaturated ketones. This method provides a facile access to differently substituted β-hydroxy α,α-difluoro ketones, versatile synthons for difluomethylated tertiary alcohols.

KW - Difluoroenoxysilanes

KW - Ketones

KW - Lewis acid catalysed

KW - Mukaiyama-aldol reaction

KW - β-Hydroxy α,α-difluoro ketones

UR - https://www.scopus.com/pages/publications/85037092183

U2 - 10.1016/j.scib.2017.10.016

DO - 10.1016/j.scib.2017.10.016

M3 - 文章

AN - SCOPUS:85037092183

SN - 2095-9273

VL - 62

SP - 1504

EP - 1509

JO - Science Bulletin

JF - Science Bulletin

IS - 22

ER -

A general and efficient Lewis acid catalysed Mukaiyama-aldol reaction of difluoroenoxysilanes and ketones

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