biostudies-literature00540Phipps EJTNIGMS NIH HHS6807-6811https://www.ebi.ac.uk/biostudies/studies/S-EPMC6980370biostudies-literatureUnknown141(17)We have developed a Rh(III)-catalyzed diastereoselective [2+1] annulation onto allylic alcohols initiated by alkenyl C-H activation of N-enoxyphthalimides to furnish substituted cyclopropyl-ketones. Notably, the traceless oxyphthalimide handle serves three functions: directing C-H activation, oxidation of Rh(III), and, collectively with the allylic alcohol, in directing cyclopropanation to control diastereoselectivity. Allylic alcohols are shown to be highly reactive olefin coupling partners leading to a directed diastereoselective cyclopropanation reaction, providing products not accessible by other routes.Journal of the American Chemical SocietyRh(III)-Catalyzed C-H Activation-Initiated Directed Cyclopropanation of Allylic Alcohols.PMC6980370R01 GM080442Phipps EJTRovis T54falseRh(III)-Catalyzed C-H Activation-Initiated Directed Cyclopropanation of Allylic Alcohols.We have developed a Rh(III)-catalyzed diastereoselective [2+1] annulation onto allylic alcohols initiated by alkenyl C-H activation of N-enoxyphthalimides to furnish substituted cyclopropyl-ketones. Notably, the traceless oxyphthalimide handle serves three functions: directing C-H activation, oxidation of Rh(III), and, collectively with the allylic alcohol, in directing cyclopropanation to control diastereoselectivity. Allylic alcohols are shown to be highly reactive olefin coupling partners leading to a directed diastereoselective cyclopropanation reaction, providing products not accessible by other routes.2019-01-01T00:00:00Z2019 May2020-10-29T10:07:08Z2020-10-02T07:13:06ZS-EPMC69803703099832410.1021/jacs.9b02156