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Synlett 1991; 1991(4): 267-268
DOI: 10.1055/s-1991-20703
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lodosulfonylation of Allylboronates as an Efficient Route to Allyl Sulfones

Michel Vaultier* , Ahmed El Louzi, Souad Lafquih Titouani, Mohammed Soufiaoui
  • *Groupe de Recherche de Physicochimie Structurale, U.R.A. C.N.R.S. 704, Université de Rennes I, Avenue du Général Leclerc, F-35042 Rennes Cedex, France
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Publication Date:
07 March 2002 (online)

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p-Toluenesulfonyl iodide adds across the double bond of allylboronates (2-alkenyl-1,3,2-dioxaborolanes) leading to β-iodo-γ-p-toluenesulfonylboronates [2-(2-iodo-3-p-toluenesulfonylalkyl)-1,3,2-dioxaborolanes]. Treatment with aqueous sodium hydroxide induces a deiodoborylation and produces allyl sulfones (2-alkenyl p-tolyl sulfones) stereoselectively.