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

Takuya Hashimoto; Kohei Takino; Kazuki Hato; Keiji Maruoka

doi:10.1002/anie.201602723

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

Angew Chem Int Ed Engl. 2016 Jul 4;55(28):8081-5. doi: 10.1002/anie.201602723. Epub 2016 May 12.

Authors

Takuya Hashimoto¹, Kohei Takino¹, Kazuki Hato¹, Keiji Maruoka²

Affiliations

¹ Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502, Japan.
² Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502, Japan. maruoka@kuchem.kyoto-u.ac.jp.

PMID: 27169816
DOI: 10.1002/anie.201602723

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.

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

Publication types

Research Support, Non-U.S. Gov't