Moran Joseph, Pfeiffer Jennifer Y, Gorelsky Serge I, Beauchemin André M
Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5.
Org Lett. 2009 May 7;11(9):1895-8. doi: 10.1021/ol900292r.
The synthesis of ketonitrones from N-alkylhydroxylamines and monosubstituted allenes is accomplished via a Cope-type hydroamination reaction in moderate to good yields. Allenes also undergo a similar reaction with aqueous hydroxylamine to give oximes in excellent yield. DFT calculations support a proposed concerted, five-membered hydroamination process, and calculated transition state energies are in excellent agreement with experimental observations.
