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.gravel
usask.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
ID: J54-Y2010-3560
