A Bulky Thiyl‐Radical Catalyst for the [3+2] Cyclization of N‐Tosyl Vinylaziridines and Alkenes. Issue 28 (12th May 2016)

• Record Type: Journal Article
• Authors: Hashimoto, Takuya; Takino, Kohei; Hato, Kazuki; Maruoka, Keiji
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 28(2016)
• Page Start: 8081
• Page End: 8085
• Publication Date: 2016-05-12
• Subjects: pyrrolidines -- radical reactions -- sulfur -- thiyl radicals -- vinylaziridines; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201602723
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : Bulk it up : A thiyl‐radical‐catalyzed cyclization reaction of N ‐tosyl vinylaziridines and alkenes was developed as a new synthetic method for the generation of substituted pyrrolidines (see scheme). The key to making this process accessible to a broad range of substrates is the use of a sterically demanding thiyl radical to prevent the undesired degradation of the catalyst.