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Rh(III)-Catalyzed C-H Activation-Initiated Directed Cyclopropanation of Allylic Alcohols

Erik J. T. Phipps, Tomislav Rovis*

*Department of Chemistry, Columbia University, New York, New York 10027, United States, Email: tr2504columbia.edu

E. J. T. Phipps, T. Rovis, J. Am. Chem. Soc., 2019, 141, 6808-6811.

DOI: 10.1021/jacs.9b02156 (free Supporting Information)



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Abstract

A Rh(III)-catalyzed diastereoselective [2+1] annulation of allylic alcohols with N-enoxyphthalimides provides substituted cyclopropyl-ketones. Notably, the traceless oxyphthalimide handle serves three functions: directing C-H activation, oxidation of Rh(III), and controlling diastereoselectivity collectively with the allylic alcohol.

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Cp*CF3



Key Words

cyclopropanes


ID: J48-Y2019