Cu(I)-Binaphthyldiimine Catalyzed Asymmetric Cyclopropanation of Olefin with Diazoacetate

Hiroyuki Suga; Tomomi Fudo; Toshikazu Ibata

doi:10.1055/s-1998-1824

Synlett 1998; 1998(8): 933-935
DOI: 10.1055/s-1998-1824

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Cu(I)-Binaphthyldiimine Catalyzed Asymmetric Cyclopropanation of Olefin with Diazoacetate

Hiroyuki Suga^* , Tomomi Fudo, Toshikazu Ibata

^*Department of Chemistry, Graduate School of Science, Osaka University, Osaka 560, Japan

Abstract

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Chiral 1,1′-binaphthyl-N,N′-bis(2,6-dichloro-benzy-lidene)-2,2′-diamine (1) was found to be an effective ligand for the copper-catalyzed enantioselective cyclopropanation of olefin with l-menthyl diazoacetate. For example, the reaction of 1,1-diphenylethylene with l-menthyl diazoacetate in the presence of CuOTf-1 complex in CH₂Cl₂ at -40 °C gave the corresponding cyclopropanecarboxylate in 98% ee.

asymmetric cyclopropanation - enantioselective synthesis - chiral copper catalyst - carbenoid - diazoacetate

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