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

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

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 con...

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Main Authors: Chi, Robin Yonggui, Jin, Zhichao, Xu, Jianfeng, Yang, Song, Song, Bao-An
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2014
Subjects:
DRNTU::Science::Chemistry::Organic chemistry
Online Access:https://hdl.handle.net/10356/104216
http://hdl.handle.net/10220/19451
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1042162020-03-07T12:34:58Z Enantioselective sulfonation of enones with sulfonyl imines by cooperative N-heterocyclic-carbene/thiourea/tertiary-amine multicatalysis Chi, Robin Yonggui Jin, Zhichao Xu, Jianfeng Yang, Song Song, Bao-An School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry 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. 2014-05-26T02:44:32Z 2019-12-06T21:28:33Z 2014-05-26T02:44:32Z 2019-12-06T21:28:33Z 2013 2013 Journal Article Jin, Z., Xu, J., Yang, S., Song, B.-A. & Chi, Y. R. (2013). Enantioselective Sulfonation of Enones with Sulfonyl Imines by Cooperative N-Heterocyclic-Carbene/Thiourea/Tertiary-Amine Multicatalysis. Angewandte Chemie International Edition, 52(47), 12354–12358. 1433-7851 https://hdl.handle.net/10356/104216 http://hdl.handle.net/10220/19451 10.1002/anie.201305023 179783 en Angewandte Chemie international edition © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
topic DRNTU::Science::Chemistry::Organic chemistry
spellingShingle DRNTU::Science::Chemistry::Organic chemistry
Chi, Robin Yonggui
Jin, Zhichao
Xu, Jianfeng
Yang, Song
Song, Bao-An
Enantioselective sulfonation of enones with sulfonyl imines by cooperative N-heterocyclic-carbene/thiourea/tertiary-amine multicatalysis
description 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.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Chi, Robin Yonggui
Jin, Zhichao
Xu, Jianfeng
Yang, Song
Song, Bao-An
format Article
author Chi, Robin Yonggui
Jin, Zhichao
Xu, Jianfeng
Yang, Song
Song, Bao-An
author_sort Chi, Robin Yonggui
title Enantioselective sulfonation of enones with sulfonyl imines by cooperative N-heterocyclic-carbene/thiourea/tertiary-amine multicatalysis
title_short Enantioselective sulfonation of enones with sulfonyl imines by cooperative N-heterocyclic-carbene/thiourea/tertiary-amine multicatalysis
title_full Enantioselective sulfonation of enones with sulfonyl imines by cooperative N-heterocyclic-carbene/thiourea/tertiary-amine multicatalysis
title_fullStr Enantioselective sulfonation of enones with sulfonyl imines by cooperative N-heterocyclic-carbene/thiourea/tertiary-amine multicatalysis
title_full_unstemmed Enantioselective sulfonation of enones with sulfonyl imines by cooperative N-heterocyclic-carbene/thiourea/tertiary-amine multicatalysis
title_sort enantioselective sulfonation of enones with sulfonyl imines by cooperative n-heterocyclic-carbene/thiourea/tertiary-amine multicatalysis
publishDate 2014
url https://hdl.handle.net/10356/104216
http://hdl.handle.net/10220/19451
_version_ 1681039781781307392

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