Rh(III)-Catalyzed Cyclopropanation Initiated by C−H Activation: Ligand Development Enables a Diastereoselective [2 + 1] Annulation

Content Provider	CiteSeerX
Author	Piou, Tiffany Rovis, Tomislav
Abstract	ABSTRACT: N-Enoxyphthalimides undergo a Rh(III)-catalyzed C−H activation initiated cyclopropanation of electron deficient alkenes. The reaction is proposed to proceed via a directed activation of the olefinic C−H bond followed by two migratory insertions, first across the electron-deficient alkene and then by cyclization back onto the enol moiety. A newly designed isopropylcyclopenta-dienyl ligand drastically improves yield and diastereose-lectivity. Rh(III) mediated C−H activation has proven to be a powerful approach for the synthesis of nitrogen containing heterocycles.1 Building on a foundation of reactivity first described by Miura and Satoh2 and Fagnou,3 we4 and others5 reported the coupling of benzamides with alkynes to form isoquinolones via Rh(III) C−H activation.6,7 Seminal work by Fagnou8 and Glorius9
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