A Novel Rhodium-Catalyzed Reduction–Oxidation Process: Reaction of 4-Alkynals with Phenol to Provide cis-4-Alkenoates


  • Support has been provided by Mitsubishi Chemical (postdoctoral fellowship support for K.T.), Bristol-Myers Squibb, Novartis, and Pfizer. Funding for the MIT Department of Chemistry Instrumentation Facility has been provided in part by NSF CHE-9808061 and NSF DBI-9729592.


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Two complementary transformations in one go: A rhodium-catalyzed transformation has been developed in which a phenol reacts with a 4-alkynal to furnish a cis-4-alkenoate in good yield (see scheme; dppe=1,2-bis(diphenylphosphino)ethene). This novel tandem process couples the reduction of an alkyne to an alkene with the oxidation of an aldehyde to an ester.