Carbonylative ring opening of terminal epoxides at atmospheric pressure |
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Authors: | Denmark Scott E Ahmad Moballigh |
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Institution: | Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu |
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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. |
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