Download PDF
Synfacts 2009(11): 1252-1252  
DOI: 10.1055/s-0029-1218121
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium-Catalyzed Formation of syn-α-Allenols

Contributor(s): Mark Lautens, David A. Candito
T. Miura, M. Shimada, P. de Mendoza, C. Deutsch, N. Krause, M. Murakami*
Kyoto University, Japan and Dortmund University of Technology, Germany
Further Information

Publication History

Publication Date:
22 October 2009 (online)

    Permissions and Reprints

Significance

Typically the addition of organometallic species to alkynyl oxiranes has provided anti-configured allenols, with reports of the alternate syn-stereochemistry being limited. The authors disclose the rhodium-catalyzed addition of boronic acids to alkynyl oxiranes, stereoselectively providing syn-allenols. The authors demonstrate the utility of this methodology in the concise synthesis of ()-boivinisnin B.