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A New Synthesis of 2-[(Dialkylcarbamoyl)Methylene]Tetrahydrofuran Derivatives by Pd-Catalyzed Oxidative Aminocarbonylation of 4-yn-1-ols

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Abstract:

A novel synthesis of 2-[(dialkylcarbamoyl)methylene]tetrahydrofuran derivatives 3-8 by Pd-catalyzed oxidative carbonylation of 4-yn-1-ols 1 in the presence of dialkylamines 2 is reported (2:1 molar ratio = 2). Reactions are carried out in 1,2- dimethoxyethane (DME) at 100°C and under 20 atm (at 25°C) of a 4:1 mixture of CO and air, in the presence of catalytic amounts of PdI2 (1 mol % with respect to 1) in conjunction with 10 equiv. of KI. Formation of 3-8 occurs through Pd-catalyzed oxidative monoaminocarbonylation of the triple bond of 1 to give 6-hydroxy-2-ynamide intermediates 9, followed by stereoselective conjugate addition of the hydroxyl group to the triple bond.

Keywords: aminocarbonylation; carbonylation; methylene]tetrahydrofurans; palladium

Document Type: Review Article

DOI: http://dx.doi.org/10.2174/1570178043488437

Affiliations: Dipartimento di Scienze Farmaceutiche, Universita della Calabria, 87036 Arcavacata di Rende, Cosenza, Italy.

Publication date: April 1, 2004

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  • Letters in Organic Chemistry publishes original letters on all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is placed on publishing quality papers very rapidly. Letters are processed rapidly and take full advantage of the Internet technology both for the submission and the review of the manuscripts.
    The journal is essential reading for all organic chemists both in academia and industry.

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