Carbonylative ring opening of terminal epoxides at atmospheric pressure.
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.
Denmark
Scott E
SE
Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu
Ahmad
Moballigh
M
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
D004852:Epoxy Compounds; D004952:Esters; D003035:Cobalt; D002248:Carbon Monoxide