Synthesis of Nitrogen Heterocycles via Directed Carbonylative C-C Bond Activation of Cyclopropanes
Andrew G Dalling1, John F Bower2
1School of Chemistry, University of Bristol Bristol, BS8 1TS, United Kingdom.
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 π-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.
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