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Article Abstract

Internal allenes are challenging substrates in copper-catalyzed borylative difunctionalization. When internal allenes featuring a methylidenecyclobutane motif were employed, a copper-catalyzed hydrofunctionalization reaction using diborons and ketones as reaction partners in the presence of a chiral monophosphorus ligand was developed, affording a series of unsaturated chiral tertiary alcohols preserving the methylidenecyclobutane motif in high regio- and stereoselectivities. Control experiments suggest that the reaction involves a boronation-deboronation process, and a plausible mechanism has been proposed.

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http://dx.doi.org/10.1021/acs.orglett.5c01718DOI Listing

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