PDF herunterladen
Synfacts 2011(5): 0524-0524  
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

Contributor(s): Mark Lautens, Jane Panteleev
Y. Sasaki, Y. Horita, C. Zhong, M. Sawamura, H. Ito*
Hokkaido University, Sapporo and PRESTO, Japan Science and Technology Agency, Saitama, Japan
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
15. April 2011 (online)

    Lizenzen und Reprints

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.