American Chemical Society
jo6b01508_si_001.pdf (5.48 MB)

Regiodivergent Ring-Opening Reaction of Trichloromethylcyclopropane Carboxylates

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journal contribution
posted on 2016-08-03, 00:00 authored by Nobuyoshi Doi, Norihiko Takeda, Okiko Miyata, Masafumi Ueda
Reagent-controlled regiodivergent ring-opening reactions of trichloromethylcyclopropane carboxylates have been developed. The regioselectivity of bond cleavage is completely controlled by the proper choice of silver salts; the treatment of trichloromethylcyclopropane with AgBF4 led to C2–C3 bond cleavage and fluorination to afford fluorinated β,γ-unsaturated ester with high stereoselectivity, while the reaction with AgOAc in THF gave a γ,δ-unsaturated ester through the reductive cleavage of the C1–C2 bond.