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Chem Soc Rev. 2011 Apr;40(4):1857-69. doi: 10.1039/c0cs00217h. Epub 2011 Mar 1.

Guiding principles for site selective and stereoselective intermolecular C-H functionalization by donor/acceptor rhodium carbenes.

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NSF Center for Stereoselective C-H Functionalization, Emory University, Department of Chemistry, Atlanta, GA, USA.


This tutorial review presents a description of the controlling elements of intermolecular C-H functionalization by means of C-H insertion by donor/acceptor rhodium carbenes. These rhodium carbenes, readily derived from the combination of diazo compounds with dirhodium(ii) catalysts, are sufficiently reactive to undergo a wide range of C-H insertions. They are also capable of highly selective reactions, controlled by a combination of steric and electronic factors. An overview of the structural factors that influence site selectivity will be given, followed by a description of the exceptional diastereo- and enantioselectivity that can be achieved. Several examples will be shown of how this methodology can be applied to streamline the synthesis of natural products and pharmaceutical targets.

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