The radical addition of alkenes catalyzed by transition metal redox systems is a class of highly synthetically useful transformations. Despite the significant development in this area over the past several decades, catalyst-controlled enantioselective functionalization of the radical intermediates involved in such transformations has long been elusive. We recently reported a copper-catalyzed method for the efficient enantioselective oxytrifluoromethylation of alkenes. Mechanistic investigation suggests a redox-catalyzed radical addition mechanism featuring a copper-mediated enantioselective C-O bond forming step via an alkyl radical. This new synthetic method not only provides efficient access to some enantioenriched CF3-containing building blocks that are otherwise hard to synthesize, but also suggests a novel approach to enantioselective functionalization via radical intermediates.

Catalytic asymmetric alkene oxytrifluoromethylation via copper-mediated enantioselective functionalization of radical intermediates

248th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.