Sulfur dioxide mediated one-pot, three-and four-component syntheses of polyfunctional sulfonamides and sulfonic esters: study of the stereoselectivity of the ene …
LC Bouchez, SR Dubbaka, M Turks…
Index: Bouchez, Laure C.; Dubbaka, Srinivas Reddy; Turks, Maris; Vogel, Pierre Journal of Organic Chemistry, 2004 , vol. 69, # 19 p. 6413 - 6418
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Citation Number: 39
Abstract
The 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 ...
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