Carbonylative ring opening of terminal epoxides at atmospheric pressure

Scott E Denmark, Moballigh Ahmad

Research output: Contribution to journalArticle

Abstract

(Chemical Equation Presented) 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.

Original languageEnglish (US)
Pages (from-to)9630-9634
Number of pages5
JournalJournal of Organic Chemistry
Volume72
Issue number25
DOIs
StatePublished - Dec 7 2007

ASJC Scopus subject areas

  • Organic Chemistry

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