3 years ago

Rearrangement of an Intermediate Cyclopropyl Ketene in a RhII-Catalyzed Formal [4 + 1]-Cycloaddition Employing Vinyl Ketenes as 1,4-Dipoles and Donor–Acceptor Metallocarbenes

Rearrangement of an Intermediate Cyclopropyl Ketene in a RhII-Catalyzed Formal [4 + 1]-Cycloaddition Employing Vinyl Ketenes as 1,4-Dipoles and Donor–Acceptor Metallocarbenes
Brandon L. Ashfeld, Tiffany A. Toni, Kevin X. Rodriguez, Nicolai Kaltwasser
A RhII-catalyzed formal [4 + 1]-cycloaddition approach toward spirooxindole cyclopentenones is described. The diastereoselective cyclopropanation of vinyl ketenes with diazooxindoles as C1 synthons initiated a relatively mild formal [1,3]-migration of an intermediate cyclopropyl ketene to provide spirooxindoles in good to excellent yields (36–99%).

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00618

DOI: 10.1021/acs.orglett.7b00618

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