Rhodium-Catalyzed Reaction of Alkynyl Oxiranes with Arylboronic Acids
T. Miura, M. Shimada, S.-Y. Ku, T. Tamai, M. Murakami*
Kyoto University, Japan
22. November 2007 (online)
The stereoselective synthesis of α-allenols is described. The authors show that arylboronic acids as well as MeMgCl fare well as nucleophiles. A variety of alkynyl oxiranes are suitable giving the syn-configured α-allenols. The reaction proceeds through a SN2′-type mechanism. Coordination of the rhodium with the oxirane oxygen is believed to be a reason for the observed high diastereoselectivity.