Literature DB >> 22058006

Designing N-heterocyclic carbenes: simultaneous enhancement of reactivity and enantioselectivity in the asymmetric hydroacylation of cyclopropenes.

Fan Liu1, Xavier Bugaut, Michael Schedler, Roland Fröhlich, Frank Glorius.   

Abstract

Faster, higher, stronger! The N-heterocyclic carbene (NHC) catalyzed diastereo- and enantioselective hydroacylation of cyclopropenes affords structurally valuable acylcyclopropanes. A new family of electron-rich, 2,6-dimethoxyphenyl-substituted NHCs induces excellent reactivity and enantioselectivity. Preliminary kinetic studies unambiguously demonstrated the superiority of this family of catalysts over known NHCs in this challenging transformation.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2011        PMID: 22058006     DOI: 10.1002/anie.201106155

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


  8 in total

Review 1.  Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

Authors:  Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal:  Chem Rev       Date:  2015-05-20       Impact factor: 60.622

2.  Carbene-Catalyzed Enantioselective Decarboxylative Annulations to Access Dihydrobenzoxazinones and Quinolones.

Authors:  Ansoo Lee; Joshua L Zhu; Taisiia Feoktistova; Alexander C Brueckner; Paul H-Y Cheong; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-27       Impact factor: 15.336

3.  Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates.

Authors:  Yujing Zhou; Jeffrey S Bandar; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2017-06-06       Impact factor: 15.419

4.  N-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes.

Authors:  Lisa Candish; Alison Levens; David W Lupton
Journal:  Chem Sci       Date:  2015-01-26       Impact factor: 9.825

5.  Regioselective hydroacylation of 1,3-dienes by cobalt catalysis.

Authors:  Qing-An Chen; Daniel K Kim; Vy M Dong
Journal:  J Am Chem Soc       Date:  2014-03-03       Impact factor: 15.419

6.  Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids.

Authors:  Jeffrey S Bandar; Erhad Ascic; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2016-04-29       Impact factor: 15.419

7.  Pd-Catalyzed Enantioselective Hydroalkynylation of Cyclopropenes.

Authors:  Longyang Dian; Ilan Marek
Journal:  ACS Catal       Date:  2019-12-26       Impact factor: 13.084

8.  Desymmetrization of unactivated bis-alkenes via chiral Brønsted acid-catalysed hydroamination.

Authors:  Zhang-Long Yu; Yong-Feng Cheng; Na-Chuan Jiang; Jian Wang; Li-Wen Fan; Yue Yuan; Zhong-Liang Li; Qiang-Shuai Gu; Xin-Yuan Liu
Journal:  Chem Sci       Date:  2020-05-20       Impact factor: 9.825

  8 in total

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