jo049047j_si_001.pdf (569.01 kB)
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
journal contribution
posted on 2004-09-17, 00:00 authored by Laure C. Bouchez, Srinivas Reddy Dubbaka, Māris Turks, Pierre VogelThe ene reaction of sulfur dioxide with enoxysilanes or with allylsilanes generates silyl sulfinates
that can be brominated (Br2 or NBS) or chlorinated (NCS or Cl2) 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.