title: Guiding principles for site selective and stereoselective intermolecular C-H functionalization by donor/acceptor rhodium carbenes.
abstract: 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.
authors.affiliation: NSF Center for Stereoselective C-H Functionalization, Emory University, Department of Chemistry, Atlanta, GA, USA. hmdavie@emory.edu
authors.forename: Huw M L
authors.initials: HM
authors.lastname: Davies
authors.forename: Daniel
authors.initials: D
authors.lastname: Morton
mesh_terms: D001391:Azo Compounds / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001391:Azo Compounds; D001688:Biological Products; C030011:carbene; D002244:Carbon; D006859:Hydrogen; D012238:Rhodium; D008697:Methane