Literature DB >> 23231752

Diastereoselective synthesis of CF3-substituted, epoxide-fused heterocycles with β-(trifluoromethyl)vinylsulfonium salts.

Sven P Fritz1, Thomas H West, Eoghan M McGarrigle, Varinder K Aggarwal.   

Abstract

CF(3)-substituted vinyl diphenylsulfonium triflate is an effective annulation reagent for the formation of α-CF(3) substituted, epoxide-fused heterocycles (pyrrolidines, piperidines, and tetrahydrofurans). This simple method affords a variety of valuable heterocyclic building blocks in a highly diastereoselective manner (dr >20:1).

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Year:  2012        PMID: 23231752     DOI: 10.1021/ol303200n

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

1.  Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors:  Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal:  Chem Rev       Date:  2019-06-25       Impact factor: 60.622

2.  α-Functionalisation of Ketones Through Metal-Free Electrophilic Activation.

Authors:  Wojciech Zawodny; Christopher J Teskey; Magdalena Mishevska; Martin Völkl; Boris Maryasin; Leticia González; Nuno Maulide
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-11       Impact factor: 15.336

Review 3.  Recent Developments in Vinylsulfonium and Vinylsulfoxonium Salt Chemistry.

Authors:  Mukulesh Mondal; Shi Chen; Nessan J Kerrigan
Journal:  Molecules       Date:  2018-03-23       Impact factor: 4.411

Review 4.  Synthesis of Substituted α-Trifluoromethyl Piperidinic Derivatives.

Authors:  Sarah Rioton; Domingo Gomez Pardo; Janine Cossy
Journal:  Molecules       Date:  2017-03-19       Impact factor: 4.411

5.  Trisubstituted 2-trifluoromethyl pyrrolidines via catalytic asymmetric Michael addition/reductive cyclization.

Authors:  Michael T Corbett; Qihai Xu; Jeffrey S Johnson
Journal:  Org Lett       Date:  2014-04-18       Impact factor: 6.005

  5 in total

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