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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Regiodivergent Ring-Opening Reaction of Trichloromethylcyclopropane Carboxylates
Nobuyoshi Doi1, Norihiko Takeda1, Okiko Miyata1
1Kobe Pharmaceutical University Motoyamakita, Higashinada, Kobe 658-8558, Japan.
Abstract:
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.
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