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Synlett 1993; 1993(9): 638-640
DOI: 10.1055/s-1993-22553
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Asymmetric Cyclopropanation of E-Olefins Using a Copper Complex of an Optically Active Bipyridine as a Catalyst

Katsuji Ito* , Tsutomu Katsuki
  • *Department of Chemistry, Faculty of Science, Kyushu University 33, Hakozaki, Higashi-ku, Fukuoka 812, Japan
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Publication Date:
19 March 2002 (online)

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Cyclopropanation of E-olefins with diazoacetate in the presence of the copper complex of C2-symmetric bipyridine (3) was found to give the corresponding cis-cyclopropanecarboxylates of good to high optical purities as major products, differing from the reaction with copper complex of structurally similar bis(oxazolines). For example, the Cyclopropanation of trans-ß-methylstyrene and trans-anethole with t-butyl diazoacetate gave the corresponding cis-isomers of >99% ee as major products, respectively.