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Synfacts 2011(5): 0524-0524
DOI: 10.1055/s-0030-1259831
DOI: 10.1055/s-0030-1259831
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Selective Hydroboration of 1,3-Enynes Containing Internal Alkynes
Y. Sasaki, Y. Horita, C. Zhong, M. Sawamura, H. Ito*
Hokkaido University, Sapporo and PRESTO, Japan Science and Technology Agency, Saitama, Japan
Further Information
Publication History
Publication Date:
15 April 2011 (online)
Significance
A regio- and stereoselective synthesis of alkyl- and alkenylboronates is disclosed. The authors utilize a copper-phosphine catalyst and obtain boronic esters selectively under substrate and ligand control. The utility of the products is further exemplified by palladium-catalyzed cross-coupling reactions and Diels-Alder cycloaddition. The observed products of this hydroboration differ from the previous reports of similar hydroboration reactions with enynes. Notably, internal alkynes can be used effectively, which are a difficult substrate class for this transformation.