Organic letters

Ketonitrones via cope-type hydroamination of allenes

…, JY Pfeiffer, SI Gorelsky, AM Beauchemin

Index: Moran, Joseph; Gorelsky, Serge I.; Dimitrijevic, Elena; Lebrun, Marie-Eve; Bedard, Anne-Catherine; Seguin, Catherine; Beauchemin, Andre M. Journal of the American Chemical Society, 2008 , vol. 130, # 52 p. 17893 - 17906

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Citation Number: 26

Abstract

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 ...