Literature DB >> 27064419

A Chiral Electrophilic Selenium Catalyst for Highly Enantioselective Oxidative Cyclization.

Yu Kawamata1, Takuya Hashimoto1, Keiji Maruoka1.   

Abstract

Chiral electrophilic selenium catalysts have been applied to catalytic asymmetric transformations of alkenes over the past two decades. However, highly enantioselective reactions with a broad substrate scope have not yet been developed. We report the first successful example of this reaction employing a catalyst based on a rigid indanol scaffold, which can be easily synthesized from a commercially available indanone. The reaction efficiently converts β,γ-unsaturated carboxylic acids into various enantioenriched γ-butenolides under mild conditions.

Entities:  

Year:  2016        PMID: 27064419     DOI: 10.1021/jacs.6b01462

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


  9 in total

1.  Organoselenium-catalyzed enantioselective syn-dichlorination of unbiased alkenes.

Authors:  Bradley B Gilbert; Stanley T-C Eey; Pavel Ryabchuk; Olivia Garry; Scott E Denmark
Journal:  Tetrahedron       Date:  2019-06-01       Impact factor: 2.457

Review 2.  Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones.

Authors:  Bin Mao; Martín Fañanás-Mastral; Ben L Feringa
Journal:  Chem Rev       Date:  2017-06-22       Impact factor: 60.622

3.  Regiocontrolled allylic functionalization of internal alkene via selenium-π-acid catalysis guided by boron substitution.

Authors:  Ling Yang; Yuan Liu; Wen-Xin Fan; Dong-Hang Tan; Qingjiang Li; Honggen Wang
Journal:  Chem Sci       Date:  2022-04-22       Impact factor: 9.969

4.  Catalytic, Enantioselective syn-Diamination of Alkenes.

Authors:  Zhonglin Tao; Bradley B Gilbert; Scott E Denmark
Journal:  J Am Chem Soc       Date:  2019-11-19       Impact factor: 15.419

5.  Guiding a divergent reaction by photochemical control: bichromatic selective access to levulinates and butenolides.

Authors:  Revannath L Sutar; Saumik Sen; Or Eivgi; Gal Segalovich; Igor Schapiro; Ofer Reany; N Gabriel Lemcoff
Journal:  Chem Sci       Date:  2017-12-18       Impact factor: 9.825

6.  Reaction of bis[(2-chlorocarbonyl)phenyl] Diselenide with Phenols, Aminophenols, and Other Amines towards Diphenyl Diselenides with Antimicrobial and Antiviral Properties.

Authors:  Mirosław Giurg; Anna Gołąb; Jakub Suchodolski; Rafał Kaleta; Anna Krasowska; Egbert Piasecki; Magdalena Piętka-Ottlik
Journal:  Molecules       Date:  2017-06-12       Impact factor: 4.411

Review 7.  Electrophilic Selenium Catalysis with Electrophilic N-F Reagents as the Oxidants.

Authors:  Ruizhi Guo; Lihao Liao; Xiaodan Zhao
Journal:  Molecules       Date:  2017-05-19       Impact factor: 4.411

8.  Cooperative Palladium/Isothiourea Catalyzed Enantioselective Formal (3+2) Cycloaddition of Vinylcyclopropanes and α,β-Unsaturated Esters.

Authors:  Jacqueline Bitai; Alastair J Nimmo; Alexandra M Z Slawin; Andrew D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-28       Impact factor: 16.823

9.  A Desilylative Approach to Alkyl Substituted C(1)-Ammonium Enolates: Application in Enantioselective [2+2] Cycloadditions.

Authors:  Yihong Wang; Claire M Young; Honglei Liu; Will C Hartley; Max Wienhold; David B Cordes; Alexandra M Z Slawin; Andrew D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2022-08-08       Impact factor: 16.823

  9 in total

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