Synfacts 2010(8): 0906-0906  
DOI: 10.1055/s-0030-1257781
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed Selective Aryl-Allyl Coupling

Contributor(s): Mark Lautens, Jane Panteleev
H. Ohmiya*, N. Yokokawa, M. Sawamura*
Hokkaido University, Sapporo, Japan
Further Information

Publication History

Publication Date:
22 July 2010 (online)

Significance

The authors disclose a copper-­catalyzed addition of boronic esters to (Z)-allyl­phosphates. Transformations similar to this are common under palladium catalysis, but selective copper-mediated examples are rare. The yields of this reaction vary from moderate to good, but the E/Z selectivities and regiocontrol are excellent. When using non-racemic starting materials, the chirality is effectively transferred to the newly formed stereocenter with almost no degradation of ee.