Literature DB >> 25651161

N-heterocyclic carbene-catalyzed radical reactions for highly enantioselective β-hydroxylation of enals.

Yuexia Zhang1, Yu Du, Zhijian Huang, Jianfeng Xu, Xingxing Wu, Yuhuang Wang, Ming Wang, Song Yang, Richard D Webster, Yonggui Robin Chi.   

Abstract

An N-heterocyclic carbene-catalyzed β-hydroxylation of enals is developed. The reaction goes through a pathway involving multiple radical intermediates, as supported by experimental observations. This oxidative single-electron-transfer reaction allows for highly enantioselective access to β-hydroxyl esters that are widely found in natural products and bioactive molecules.

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Year:  2015        PMID: 25651161     DOI: 10.1021/ja511371a

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  20 in total

1.  High-throughput photocapture approach for reaction discovery.

Authors:  Alison A Bayly; Benjamin R McDonald; Milan Mrksich; Karl A Scheidt
Journal:  Proc Natl Acad Sci U S A       Date:  2020-06-01       Impact factor: 11.205

2.  Rhodium-Catalyzed Enantioselective Radical Addition of CX4 Reagents to Olefins.

Authors:  Bo Chen; Cheng Fang; Peng Liu; Joseph M Ready
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-14       Impact factor: 15.336

3.  Single-electron Carbene Catalysis in Redox Processes.

Authors:  Anna V Bay; Karl A Scheidt
Journal:  Trends Chem       Date:  2022-02-11

4.  Synthesis of Highly Congested Tertiary Alcohols via the [3,3] Radical Deconstruction of Breslow Intermediates.

Authors:  Roger Machín Rivera; Nikolas R Burton; Luke D Call; Marshall A Tomat; Vincent N G Lindsay
Journal:  Org Lett       Date:  2022-06-03       Impact factor: 6.072

5.  Three-component carboacylation of alkenes via cooperative nickelaphotoredox catalysis.

Authors:  Dingyi Wang; Lutz Ackermann
Journal:  Chem Sci       Date:  2022-05-30       Impact factor: 9.969

6.  Oxidatively Initiated NHC-Catalyzed Enantioselective Synthesis of 3,4-Disubstituted Cyclopentanones from Enals.

Authors:  Nicholas A White; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2015-08-10       Impact factor: 15.419

7.  Critical Assessment of the Reducing Ability of Breslow-type Derivatives and Implications for Carbene-Catalyzed Radical Reactions*.

Authors:  Ludivine Delfau; Samantha Nichilo; Florian Molton; Julie Broggi; Eder Tomás-Mendivil; David Martin
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-15       Impact factor: 16.823

Review 8.  Recent advances in N-heterocyclic carbene-based radical catalysis.

Authors:  Takuya Ishii; Kazunori Nagao; Hirohisa Ohmiya
Journal:  Chem Sci       Date:  2020-05-11       Impact factor: 9.825

Review 9.  Light opens a new window for N-heterocyclic carbene catalysis.

Authors:  Jing Liu; Xiao-Ning Xing; Jin-Hai Huang; Liang-Qiu Lu; Wen-Jing Xiao
Journal:  Chem Sci       Date:  2020-08-11       Impact factor: 9.825

10.  Light-Driven Carbene Catalysis for the Synthesis of Aliphatic and α-Amino Ketones.

Authors:  Anna V Bay; Keegan P Fitzpatrick; Gisela A González-Montiel; Abdikani Omar Farah; Paul Ha-Yeon Cheong; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-14       Impact factor: 16.823

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