Bismuth(III) triflate promoted intramolecular hydroamination of unactivated alkenyl sulfonamides in the preparation of pyrrolidines

František Mathia; Peter Szolcsányi

doi:10.1039/c2ob07064b

Bismuth(III) triflate promoted intramolecular hydroamination of unactivated alkenyl sulfonamides in the preparation of pyrrolidines

Org Biomol Chem. 2012 Apr 14;10(14):2830-9. doi: 10.1039/c2ob07064b. Epub 2012 Feb 29.

Authors

František Mathia¹, Peter Szolcsányi

Affiliation

¹ Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovakia.

PMID: 22373546
DOI: 10.1039/c2ob07064b

Abstract

Bi(OTf)(3)·nH(2)O was found to be an efficient promoter of the cyclisative hydroamination of unactivated alkenyl sulfonamides, giving rise to the N-protected 2-methyl pyrrolidines in good to excellent yields (up to 95%). Based on control experiments, a joint Lewis acid-Brønsted acid catalysis might be in operation, or triflic acid itself, generated in situ by hydrolysis of metal triflate, could be the true hydroamination catalyst.