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

Authors

  • Vincent Darmency
  • Philippe Renaud

DOI:

https://doi.org/10.2533/000942905777676722

Keywords:

Alkylation, Enamides, Hydroboration, Organoboranes, Radical reactions, Sulfonamides

Abstract

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 ?-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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Published

2005-03-01