Literature DB >> 24782343

Catalytic enantioselective inverse electron demand hetero-Diels-Alder reaction with allylsilanes.

Yuki Matsumura1, Takahiro Suzuki, Akira Sakakura, Kazuaki Ishihara.   

Abstract

The first diastereo- and enantioselective inverse electron demand hetero-Diels-Alder reaction of β,γ-unsaturated α-ketoesters with allylsilanes is described. Chiral copper(II) catalysts successfully activate the β,γ-unsaturated α-ketoesters and promote the reaction with allylsilanes with excellent enantioselectivities. This process represents a new entry to chiral oxanes.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Lewis acid; asymmetric catalysis; copper; cycloaddition; heterocycles

Year:  2014        PMID: 24782343     DOI: 10.1002/anie.201402934

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


  4 in total

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Authors:  Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal:  Chem Rev       Date:  2021-05-21       Impact factor: 60.622

2.  Triflimide-catalyzed allylsilane annulations of benzylic alcohols for the divergent synthesis of indanes and tetralins.

Authors:  Jordan C T Reddel; Weiwei Wang; Kalli Koukounas; Regan J Thomson
Journal:  Chem Sci       Date:  2016-12-09       Impact factor: 9.825

3.  Enantioselective access to tricyclic tetrahydropyran derivatives by a remote hydrogen bonding mediated intramolecular IEDHDA reaction.

Authors:  Min Jin; Congyun Tang; Yingying Li; Shuai Yang; Ying-Tao Yang; Lin Peng; Xiao-Nian Li; Wenjing Zhang; Zhili Zuo; Fabien Gagosz; Liang-Liang Wang
Journal:  Nat Commun       Date:  2021-12-10       Impact factor: 14.919

4.  Trityl Cation-Catalyzed Hosomi-Sakurai Reaction of Allylsilane with β,γ-Unsaturated α-Ketoester to Form γ,γ-Disubstituted α-Ketoesters.

Authors:  Zubao Gan; Deyun Cui; Hongyun Zhang; Ying Feng; Liying Huang; Yingying Gui; Lu Gao; Zhenlei Song
Journal:  Molecules       Date:  2022-07-24       Impact factor: 4.927

  4 in total

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