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

Authors

  • Andrew G. Dalling School of Chemistry, University of Bristol Bristol, BS8 1TS, United Kingdom
  • John F. Bower School of Chemistry, University of Bristol Bristol, BS8 1TS, United Kingdom;, Email: john.bower@bristol.ac.uk

DOI:

https://doi.org/10.2533/chimia.2018.595

Keywords:

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

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.

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Published

2018-09-01