Carbonylative ring opening of terminal epoxides at atmospheric pressure

[GRAPHICS] The carbonylative opening of terminal epoxides under mild conditions has been developed using CO2-(CO)(8) as the catalyst. Under I 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.