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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 (free Supporting Information)


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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.

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proposed mechanism



Key Words

Pyrroles


ID: J54-Y2009-1660