Enantioselective synthesis of trifluoromethylated tertiary thioethers through organocatalytic sulfa-Michael addition of thiols to β-trifluoromethyl β,β-disubstituted enones

Yao Feng Wang; Shaoxiang Wu; Pran Gopal Karmaker; Muhammad Sohail; Qi Wang; Fu Xue Chen

doi:10.1055/s-0034-1380138

Enantioselective synthesis of trifluoromethylated tertiary thioethers through organocatalytic sulfa-Michael addition of thiols to β-trifluoromethyl β,β-disubstituted enones

Yao Feng Wang, Shaoxiang Wu, Pran Gopal Karmaker, Muhammad Sohail, Qi Wang, Fu Xue Chen^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

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

14 Citations (Scopus)

Abstract

An organocatalytic asymmetric sulfa-Michael addition of thiols to β-trifluoromethyl β,β-disubstituted (E)-enones in the presence of 10 mol% of a cinchona alkaloid-derived thiourea catalyst provides direct and simple access to chiral trifluoromethyl tertiary thioethers in high yields and up to 76% ee.

Original language	English
Pages (from-to)	1147-1153
Number of pages	7
Journal	Synthesis
Volume	47
Issue number	8
DOIs	https://doi.org/10.1055/s-0034-1380138
Publication status	Published - 1 Apr 2015

Keywords

Michael additions
asymmetric catalysis
enones
organocatalysis
sulfides
thiols

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10.1055/s-0034-1380138

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title = "Enantioselective synthesis of trifluoromethylated tertiary thioethers through organocatalytic sulfa-Michael addition of thiols to β-trifluoromethyl β,β-disubstituted enones",

abstract = "An organocatalytic asymmetric sulfa-Michael addition of thiols to β-trifluoromethyl β,β-disubstituted (E)-enones in the presence of 10 mol% of a cinchona alkaloid-derived thiourea catalyst provides direct and simple access to chiral trifluoromethyl tertiary thioethers in high yields and up to 76% ee.",

keywords = "Michael additions, asymmetric catalysis, enones, organocatalysis, sulfides, thiols",

author = "Wang, {Yao Feng} and Shaoxiang Wu and Karmaker, {Pran Gopal} and Muhammad Sohail and Qi Wang and Chen, {Fu Xue}",

note = "Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart · New York.",

year = "2015",

month = apr,

day = "1",

doi = "10.1055/s-0034-1380138",

language = "English",

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TY - JOUR

T1 - Enantioselective synthesis of trifluoromethylated tertiary thioethers through organocatalytic sulfa-Michael addition of thiols to β-trifluoromethyl β,β-disubstituted enones

AU - Wang, Yao Feng

AU - Wu, Shaoxiang

AU - Karmaker, Pran Gopal

AU - Sohail, Muhammad

AU - Wang, Qi

AU - Chen, Fu Xue

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart · New York.

PY - 2015/4/1

Y1 - 2015/4/1

N2 - An organocatalytic asymmetric sulfa-Michael addition of thiols to β-trifluoromethyl β,β-disubstituted (E)-enones in the presence of 10 mol% of a cinchona alkaloid-derived thiourea catalyst provides direct and simple access to chiral trifluoromethyl tertiary thioethers in high yields and up to 76% ee.

AB - An organocatalytic asymmetric sulfa-Michael addition of thiols to β-trifluoromethyl β,β-disubstituted (E)-enones in the presence of 10 mol% of a cinchona alkaloid-derived thiourea catalyst provides direct and simple access to chiral trifluoromethyl tertiary thioethers in high yields and up to 76% ee.

KW - Michael additions

KW - asymmetric catalysis

KW - enones

KW - organocatalysis

KW - sulfides

KW - thiols

UR - http://www.scopus.com/inward/record.url?scp=84926382730&partnerID=8YFLogxK

U2 - 10.1055/s-0034-1380138

DO - 10.1055/s-0034-1380138

M3 - Article

AN - SCOPUS:84926382730

SN - 0039-7881

VL - 47

SP - 1147

EP - 1153

JO - Synthesis

JF - Synthesis

IS - 8

ER -

Enantioselective synthesis of trifluoromethylated tertiary thioethers through organocatalytic sulfa-Michael addition of thiols to β-trifluoromethyl β,β-disubstituted enones

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Keywords

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