Counterion Effects in a Gold-Catalyzed Synthesis of Pyrroles from Alkynyl Aziridines
Paul W. Davies* and Nicolas Martin
*School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT, U.K., Email: p.w.daviesbham.ac.uk
P. W. Davies, N. Martin, Org. Lett., 2009, 11, 2293-2296.
DOI: 10.1021/ol900609f
see article for more reactions
Abstract
Aryl-substituted N-tosyl alkynyl aziridines undergo a gold-catalyzed ring expansion to afford 2,5-substituted pyrrole products. Depending on the the counterion to the gold catalyst and the solvent, a ring-expansion and rearrangement leads to 2,4-substituted pyrroles.
see article for more examples
proposed mechanism
Key Words
ID: J54-Y2009-1660