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Synfacts 2010(11): 1269-1269  
DOI: 10.1055/s-0030-1258747
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Novel Asymmetric Synthesis of Substituted Cyclopropylboronates

Contributor(s): Hisashi Yamamoto, Jiajing Tan
C. Zhong, S. Kunii, Y. Kosaka, M. Sawamura, H. Ito*
Hokkaido University, Sapporo and Japan Science and Technology Agency, Saitama, Japan
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Publication History

Publication Date:
21 October 2010 (online)

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Significance

The highly enantioselective copper(I)-catalyzed synthesis of trans-aryl- and -heteroaryl-substituted cyclopropylboronates from (Z)-allylic phosphates was described. The desired products were obtained in good to excellent enantio- and diastereoselectivities and in moderate yields. Also, the authors observed a unique ligand-controlled product switch between the trans and cis configurations when (E)-allylic phosphates were used.