Literature DB >> 27169816

A Bulky Thiyl-Radical Catalyst for the [3+2] Cyclization of N-Tosyl Vinylaziridines and Alkenes.

Takuya Hashimoto1, Kohei Takino1, Kazuki Hato1, Keiji Maruoka2.   

Abstract

Thiyl-radical-catalyzed cyclization reactions of N-tosyl vinylaziridines and alkenes were developed as a new synthetic method for the generation of substituted pyrrolidines. The key to making this process accessible to a broad range of substrates is the use of a sterically demanding thiyl radical, which prevents the undesired degradation of the catalyst.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  pyrrolidines; radical reactions; sulfur; thiyl radicals; vinylaziridines

Year:  2016        PMID: 27169816     DOI: 10.1002/anie.201602723

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


  5 in total

Review 1.  Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors:  Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal:  Chem Rev       Date:  2021-11-23       Impact factor: 60.622

2.  Kinetic Analysis of a Cysteine-Derived Thiyl-Catalyzed Asymmetric Vinylcyclopropane Cycloaddition Reflects Numerous Attractive Noncovalent Interactions.

Authors:  Amanda K Turek; Marcus H Sak; Scott J Miller
Journal:  J Am Chem Soc       Date:  2021-09-23       Impact factor: 16.383

3.  Bromine Radical Catalysis by Energy Transfer Photosensitization.

Authors:  Dian-Feng Chen; Cameron H Chrisman; Garret M Miyake
Journal:  ACS Catal       Date:  2020-01-30       Impact factor: 13.084

Review 4.  An overview on disulfide-catalyzed and -cocatalyzed photoreactions.

Authors:  Yeersen Patehebieke
Journal:  Beilstein J Org Chem       Date:  2020-06-23       Impact factor: 2.883

Review 5.  Thiyl Radicals: Versatile Reactive Intermediates for Cyclization of Unsaturated Substrates.

Authors:  Dylan M Lynch; Eoin M Scanlan
Journal:  Molecules       Date:  2020-07-07       Impact factor: 4.411

  5 in total

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