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^*

^*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

26 Scopus citations

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.

Original language	English
Pages (from-to)	1504-1509
Number of pages	6
Journal	Science Bulletin
Volume	62
Issue number	22
DOIs	https://doi.org/10.1016/j.scib.2017.10.016
State	Published - 30 Nov 2017

Keywords

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

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10.1016/j.scib.2017.10.016

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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.",

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}

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

Abstract

Keywords

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