Organic Chemistry Portal

Abstracts

Search:

NHC-Catalyzed Intramolecular Redox Amidation for the Synthesis of Functionalized Lactams

Karen Thai, Li Wang, Travis Dudding, François Bilodeau and Michel Gravel*

*Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, SK S7N 5C9, Canada, Department of Chemistry, Brock University, St. Catharines, ON L2S 3A1 Canada, Email: michel.gravelusask.ca

K. Thai, L. Wang, T. Dudding, F. Bilodeau, M. Gravel, Org. Lett., 2010, 12, 5708-5711.

DOI: 10.1021/ol102536s


see article for more reactions

Abstract

A very efficient NHC-catalyzed ring expansion reaction cleanly furnishes five- and six-membered N-Ts and N-Bn lactams, without the need for further purification. The stoichiometric base is responsible for deprotonation of the triazolium precatalyst and activation of the nitrogen leaving group through hydrogen bonding.

see article for more examples



Key Words

δ-lactams


ID: J54-Y2010-3560