Synfacts 2007(12): 1280-1280  
DOI: 10.1055/s-2007-991352
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Reaction of Alkynyl Oxiranes with Arylboronic Acids

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
T. Miura, M. Shimada, S.-Y. Ku, T. Tamai, M. Murakami*
Kyoto University, Japan
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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.