Copper-Catalyzed Cyclopropanation of Allylic Carbonates with
Diboron

doi:10.1055/s-0028-1083615

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Synfacts 2008(12): 1300-1300
DOI: 10.1055/s-0028-1083615

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

Copper-Catalyzed Cyclopropanation of Allylic Carbonates with Diboron

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
H. Ito*, Y. Kosaka, K. Nonoyama, Y. Sasaki, M. Sawamura*
Hokkaido University, Sapporo, Japan

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Publikationsdatum:
20. November 2008 (online)

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Significance

The authors reported highly diastereo- and enantioselective cyclopropanations of γ-silylated allylic carbonates with diboron species catalyzed by copper(I). In addition, they achieved the highly enantioselective reaction with a chiral phosphine ligand. The resulting B-Si bifunctional cyclopropane was further derivatized by Suzuki-Miyaura coupling and Tamao oxidation without any loss of stereochemical purity.