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Open Access Alkylation of Ethyl Pyruvate via Reductive Coupling of Alkenes and Ethyl 2-(Benzenesulfonylamino)acrylate

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Radical coupling of B-alkylcatecholboranes, in situ generated from the corresponding alkenes, with ethyl 2-(benzenesulfonylamino)acrylate is reported. This reaction represents an extension of the radical allylation of Balkylcatecholboranes by allylsulfones. This unique process allows the preparation of various α-ketoesters (alkylated pyruvates) in a straightforward manner. It also demonstrates the generality of the radical mediated C–C bond formation starting from organoboranes and allylic benzenesulfonyl derivatives.

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Keywords: ALKYLATION; ENAMIDES; HYDROBORATION; ORGANOBORANES; RADICAL REACTIONS; SULFONAMIDES

Document Type: Research Article

Publication date: March 1, 2005

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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