Sulfur dioxide mediated one-pot, four-component synthesis of polyfunctional sulfones and sulfonamides, including medium-ring cyclic derivatives

• Published in: Tetrahedron Vol. 61; no. 48; pp. 11473 - 11487
• Main Authors: Bouchez, Laure C., Turks, Māris, Dubbaka, Srinivas Reddy, Fonquerne, Freddy, Craita, Cotinica, Laclef, Sylvain, Vogel, Pierre
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 28-11-2005
• Subjects: 1,2-Thiazonines; Ene reaction; Oxyallytion; Polyfunctional sulfonamides; Polyfunctional sulfones; Silyl sulfinates; Thiocines; Silyl sulfinates; Polyfunctional sulfones; Ene reaction; Thiocines; Oxyallytion; Polyfunctional sulfonamides; 1,2-Thiazonines
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2005.08.067

In previous papers (
Synthesis
2002, 232 and
J. Org. Chem.
2004,
69, 6413), we have shown that 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 the same pot into polyfunctional sulfones, sulfonamides or sulfonic esters. We are presenting further applications of this method, including the synthesis of new medium-size heterocyclic systems of the type tetrahydro-2
H-thiocines and hexahydro-1,2-thiazonine.
Graphical Abstract