Chemistry Letters

Another Role of Copper in the Simmons–Smith Reaction: Copper-catalyzed Nucleophilic Michael-type Cyclopropanation of α, β-Unsaturated Ketones

K Fujii, T Misaki, T Sugimura

Index: Fujii, Kanami; Misaki, Tomonori; Sugimura, Takashi Chemistry Letters, 2014 , vol. 43, # 5 p. 634 - 636

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Abstract

Cyclopropanation was performed using the Furukawa procedure with CH 2 I 2/Et 2 Zn and α, β-unsaturated ketones. The reaction was performed in the presence of a copper salt. The reactivity was highly dependent on the substrate structure, and cyclopropanated products were obtained in better yields than those achieved using the original Simmons–Smith conditions with a Zn–Cu couple in some cases. Stereospecificity was observed in a ...