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Synfacts 2010(8): 0906-0906
DOI: 10.1055/s-0030-1257781
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
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.