Synthesis of Nitrogen Heterocycles via Directed Carbonylative C–C Bond Activation of Cyclopropanes

Abstract

This review concentrates on recent developments from our laboratory concerning the Rh-catalyzed carbonylative C–C bond activation of cyclopropanes. Specifically, we have found that N-based directing groups are effective at controlling the regioselectivity of C–C bond activation during the formation of rhodacyclopentanone intermediates. These engage tethered ?-unsaturated components (e.g. alkenes) or conventional nucleophiles in cycloaddition and heterocyclization processes, respectively. Using this approach, direct and modular access to a wide range of complex heterocyclic ring systems is achieved. The review summarizes the scope of our methodologies and outlines key mechanistic features.

Keywords

• C–c bond activation
• Carbonylation
• Cycloaddition
• Cyclopropane
• Rhodium