The strong binding ability of P-ylides with transition metals limits the utilization of stabilized P-ylide as nucleophiles in asymmetric organometallic catalysis.H erein we describe the first rhodium-catalyzed asymmetric ring-opening reaction of P-ylides utilizing oxabicyclic alkenes as the electrophilic partner.V arious P-ylides including ester-, ketone-and amide-style P-ylides are all applicable.T his asymmetric reaction occurs through the cleavage of two bridgehead CÀOb onds and the formation of two CÀC bonds,a nd oxabenzonorbornadienes are used as 1,4-biselectrophiles,thus providing access to benzonorcaradienes in good yields with high enantioselectivity and perfect diastereoselectivity.T he present protocol also constitutes the first highly enantioselective direct catalytic asymmetric cyclopropanation of stabilized P-ylide nucleophiles.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under https://doi.
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