title: Carbonylative ring opening of terminal epoxides at atmospheric pressure.
abstract: The carbonylative opening of terminal epoxides under mild conditions has been developed using Co2(CO)8 as the catalyst. Under 1 atm of carbon monoxide and at room temperature in methanol, propylene oxide is converted to methyl 3-hydroxybutanoate in up to 89% yield. This transformation is general for many terminal epoxides bearing alkyl, alkenyl, aryl, alkoxy, chloromethyl, phthalimido, and acetal functional groups. The opening takes place without epimerization at the secondary stereocenter.
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu
authors.forename: Scott E
authors.initials: SE
authors.lastname: Denmark
authors.forename: Moballigh
authors.initials: M
authors.lastname: Ahmad
mesh_terms: D001274:Atmospheric Pressure; D002248:Carbon Monoxide / Q000737:chemistry*; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D004852:Epoxy Compounds; D004952:Esters; D003035:Cobalt; D002248:Carbon Monoxide