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Updated: Jun 11, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Hypervalent iodine-mediated cyclization of bishomoallylamides to prolinols
Smaher E Butt1, Konrad Kepski1, Jean-Marc Sotiropoulos2
1Department of Physical and Life Sciences, University of Huddersfield, Queensgate, Huddersfield HD1 3DH, United Kingdom.
Abstract:
A change in mechanism was observed in the hypervalent iodine-mediated cyclization of N-alkenylamides when the carbon chain between the alkene and the amide increased from two to three atoms. In the latter case, cyclization at the amide nitrogen to form the pyrrolidine ring was favored over cyclization at the amide oxygen. A DFT study was undertaken to rationalize the change in mechanism of this cyclization process. In addition, reaction conditions were developed, and the scope of this cyclization studied.
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