Enantioselective sulfonation of enones with sulfonyl imines by cooperative N-heterocyclic-carbene/thiourea/tertiary-amine multicatalysis

Zhichao Jin; Jianfeng Xu; Song Yang; Bao An Song; Yonggui Robin Chi

doi:10.1002/anie.201305023

Enantioselective sulfonation of enones with sulfonyl imines by cooperative N-heterocyclic-carbene/thiourea/tertiary-amine multicatalysis

Zhichao Jin, Jianfeng Xu, Song Yang, Bao An Song, Yonggui Robin Chi

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

96 Citations (Scopus)

Abstract

Many hands make light work: In an organocatalytic asymmetric sulfonation of enones, the activation of a sulfonyl imine by an N-heterocyclic carbene (NHC) catalyst led to the release of a sulfinic anion, which underwent nucleophilic addition to the enone. The enantioselectivity of the process was controlled by a chiral thiourea/amine co-catalyst through anion recognition and hydrogen-bonding interactions. Tol=p-tolyl.

Original language	English
Pages (from-to)	12354-12358
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	47
DOIs	https://doi.org/10.1002/anie.201305023
Publication status	Published - Nov 18 2013
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

α,β-unsaturated ketones
enantioselective sulfonation
Michael addition
N-S bond cleavage
organocatalysis

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10.1002/anie.201305023

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title = "Enantioselective sulfonation of enones with sulfonyl imines by cooperative N-heterocyclic-carbene/thiourea/tertiary-amine multicatalysis",

abstract = "Many hands make light work: In an organocatalytic asymmetric sulfonation of enones, the activation of a sulfonyl imine by an N-heterocyclic carbene (NHC) catalyst led to the release of a sulfinic anion, which underwent nucleophilic addition to the enone. The enantioselectivity of the process was controlled by a chiral thiourea/amine co-catalyst through anion recognition and hydrogen-bonding interactions. Tol=p-tolyl.",

keywords = "α,β-unsaturated ketones, enantioselective sulfonation, Michael addition, N-S bond cleavage, organocatalysis",

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T1 - Enantioselective sulfonation of enones with sulfonyl imines by cooperative N-heterocyclic-carbene/thiourea/tertiary-amine multicatalysis

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AU - Xu, Jianfeng

AU - Yang, Song

AU - Song, Bao An

AU - Chi, Yonggui Robin

PY - 2013/11/18

Y1 - 2013/11/18

N2 - Many hands make light work: In an organocatalytic asymmetric sulfonation of enones, the activation of a sulfonyl imine by an N-heterocyclic carbene (NHC) catalyst led to the release of a sulfinic anion, which underwent nucleophilic addition to the enone. The enantioselectivity of the process was controlled by a chiral thiourea/amine co-catalyst through anion recognition and hydrogen-bonding interactions. Tol=p-tolyl.

AB - Many hands make light work: In an organocatalytic asymmetric sulfonation of enones, the activation of a sulfonyl imine by an N-heterocyclic carbene (NHC) catalyst led to the release of a sulfinic anion, which underwent nucleophilic addition to the enone. The enantioselectivity of the process was controlled by a chiral thiourea/amine co-catalyst through anion recognition and hydrogen-bonding interactions. Tol=p-tolyl.

KW - α,β-unsaturated ketones

KW - enantioselective sulfonation

KW - Michael addition

KW - N-S bond cleavage

KW - organocatalysis

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ER -

Enantioselective sulfonation of enones with sulfonyl imines by cooperative N-heterocyclic-carbene/thiourea/tertiary-amine multicatalysis

Abstract

ASJC Scopus Subject Areas

Keywords

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