Sulfur dioxide mediated one-pot, three- and four-component syntheses of polyfunctional sulfonamides and sulfonic esters: study of the stereoselectivity of the ene reaction of sulfur dioxide

The Journal of Organic Chemistry
Laure C BouchezPierre Vogel

Abstract

The ene reaction of sulfur dioxide with enoxysilanes or with allylsilanes generates silyl sulfinates that can be brominated (Br(2) or NBS) or chlorinated (NCS or Cl(2)) to produce the corresponding sulfonyl halides. They react with primary and secondary amines or alcohols to give the corresponding sulfonamides and sulfonic esters, respectively. The hetero-Diels-Alder addition of sulfur dioxide to 1-oxy- or 1,3-dioxy-1,3-dienes generates zwitterions that add to enoxysilanes or allylsilanes giving silyl sulfinates that can be converted in situ into polyfunctional sulfonamides or sulfonic esters. This realizes quick access to libraries of complicated sulfonamides and sulfonic esters applying one-pot, three- and four-component methods.

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Citations

Jan 16, 2016·Organic Letters·Andy S TsaiVincent Mascitti
Feb 19, 2005·Angewandte Chemie·Diego J Ramón, Miguel Yus
Dec 17, 2014·Organic & Biomolecular Chemistry·Gang LiuJie Wu
Jun 15, 2005·Chemistry : a European Journal·Laure C Bouchez, Pierre Vogel
Jun 30, 2012·Chemical Communications : Chem Comm·Shengqing Ye, Jie Wu
Sep 5, 2012·Chemical Communications : Chem Comm·Shengqing Ye, Jie Wu
Aug 10, 2007·Accounts of Chemical Research·Pierre VogelJosé Angel Sordo
Jul 28, 2007·Organic Letters·Anirban KarMan Kin Tse

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