Thermal and high pressure intramolecular Diels-Alder reaction of vinylsulfonamides.
Vinylsulfonamides with a furan, carbocyclic, semicyclic or acyclic 1,3-diene moiety are synthetized via a domino elimination-amidation reaction of 2-chloroethanesulfonyl chloride. Intramolecular Diels-Alder reaction of these vinylsulfonamides with thermal (toluene, 110 degrees C) or high pressure (dichloromethane, 13 kbar) activation provides efficient access to a range of gamma- and delta-sultams following a 2-3 d long synthetic procedure. Enantiopure sultams are readily obtained from N-1-phenylethyl substituted vinylsulfonamides.
Rogachev
Victor O
VO
Department of Organic Chemistry, Tomsk Polytechnic University, Prospekt Lenina 30, 634050 Tomsk, Russia. victor.rogachev@web.de
Metz
Peter
P
D006358:Hot Temperature; D011312:Pressure; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D013449:Sulfonamides; D014753:Vinyl Compounds