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ORGANIC LETTERS
Volume -, Issue -, Pages -Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c04010
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In this study, a photochemical, chemoselective reaction between aryldiazoacetates and allylic alcohols was reported. This reaction efficiently furnishes cyclopropane-fused lactone skeletons in one step. The diastereoselectivity of the reaction was precisely controlled, and chemoselective cyclopropanation of allylic alcohols followed by transesterification produced a series of bicyclic lactones in high yield without the formation of ether byproducts via typical O-H insertion reactions.
Cyclopropane-fused lactones are highly desirable in drug and natural products synthesis. Herein, we report on a photochemical, chemoselective reaction of aryldiazoacetates with allylic alcohols that furnishes cyclopropane-fused lactone skeletons efficiently in one step. The diastereoselectivity of the protocol was precisely controlled, and chemoselective cyclopropanation of allylic alcohols via free carbene intermediate followed by transesterification constitutes a series of bicyclic lactones in high yield without the formation of ether byproducts via typical O- H insertion reactions.
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