Sultam synthesis via Cu-catalyzed intermolecular carboamination of alkenes with N-fluorobenzenesulfonimide

Keiichi Kaneko; Tatsuhiko Yoshino; Shigeki Matsunaga; Motomu Kanai

doi:10.1021/ol4009848

Sultam synthesis via Cu-catalyzed intermolecular carboamination of alkenes with N-fluorobenzenesulfonimide

Org Lett. 2013 May 17;15(10):2502-5. doi: 10.1021/ol4009848. Epub 2013 Apr 29.

Authors

Keiichi Kaneko¹, Tatsuhiko Yoshino, Shigeki Matsunaga, Motomu Kanai

Affiliation

¹ Graduate School of Pharmaceutical Sciences, the University of Tokyo , Hongo 7-3-1, Bunkyo-ku, Tokyo 113-0033, Japan, and ACT-C, Japan Science and Technology Agency (JST) , Hongo 7-3-1, Bunkyo-ku, Tokyo 113-0033, Japan.

PMID: 23627864
DOI: 10.1021/ol4009848

Abstract

Cu-catalyzed intermolecular carboamination of alkenes is described. The reaction of terminal alkenes and an internal alkene with N-fluorobenzenesulfonimide was promoted by 2.5 mol % of a Cu(I)-salt at 60 °C, and six-membered ring sultams were obtained in 91-44% yields.

Publication types

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

MeSH terms

Alkenes / chemistry*
Amination
Catalysis
Copper / chemistry*
Molecular Structure
Stereoisomerism
Sulfonamides / chemical synthesis*
Sulfonamides / chemistry*

Substances

Alkenes
Sulfonamides
beta-sultam
N-fluorobenzenesulfonimide
Copper