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Published on: September 8, 2013
Iridium-Catalyzed Enantioselective Allenylic Cyanomethylation
Aditya Chakrabarty1, Santanu Mukherjee1
1Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
None:
The poor acidity of acetonitrile restricted its utility as a C2 synthon of a cyanomethyl group for incorporation into organic compounds. We now employed a 2-azido allylic alcohol as an acetonitrile enolate surrogate for the first enantioselective allenylic cyanomethylation. This mild and base-free protocol utilizes cooperative iridium and Lewis acid catalysis for the activation of branched allenylic alcohols to deliver α-allenylic acetonitriles in moderate to good yields with excellent enantioselectivity.
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