Literature DB >> 24115649

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

Zhichao Jin1, Jianfeng Xu, Song Yang, Bao-An Song, Yonggui Robin Chi.   

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.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Michael addition; NS bond cleavage; enantioselective sulfonation; organocatalysis; α,β-unsaturated ketones

Mesh：

Substances：

Year:  2013        PMID： 24115649     DOI： 10.1002/anie.201305023

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  10 in total

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3.  Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids.

Authors:  Anna V Davies; Keegan P Fitzpatrick; Rick C Betori; Karl A Scheidt
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Review 4.  Dimeric Cinchona alkaloids.

Authors:  Przemysław J Boratyński
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5.  Stereoconvergent arylations and alkenylations of unactivated alkyl electrophiles: catalytic enantioselective synthesis of secondary sulfonamides and sulfones.

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Authors:  Xingkuan Chen; Hongling Wang; Kazuki Doitomi; Chong Yih Ooi; Pengcheng Zheng; Wangsheng Liu; Hao Guo; Song Yang; Bao-An Song; Hajime Hirao; Yonggui Robin Chi
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Authors:  Bruno Matos Paz; Yang Li; Mathias Kirk Thøgersen; Karl Anker Jørgensen
Journal:  Chem Sci       Date:  2017-10-02       Impact factor: 9.825

8.  Access to chiral β-sulfonyl carbonyl compounds via photoinduced organocatalytic asymmetric radical sulfonylation with sulfur dioxide.

Authors:  Fu-Sheng He; Chun Zhang; Minghui Jiang; Lujun Lou; Jie Wu; Shengqing Ye
Journal:  Chem Sci       Date:  2022-07-08       Impact factor: 9.969

9.  Highly enantioselective sulfa-Michael addition reactions using N-heterocyclic carbene as a non-covalent organocatalyst.

Authors:  Jiean Chen; Sixuan Meng; Leming Wang; Hongmei Tang; Yong Huang
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Authors:  Bo Zhu; Shuai Qiu; Jiangtao Li; Michelle L Coote; Richmond Lee; Zhiyong Jiang
Journal:  Chem Sci       Date:  2016-06-09       Impact factor: 9.825
  10 in total

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