Regio- and stereospecific synthesis of beta-sulfonamidodisulfides and beta-sulfonamidosulfides from aziridines using tetrathiomolybdate as a sulfur transfer reagent.
A comprehensive study of a general and effective one-step procedure for the synthesis of beta-sulfonamidodisulfides directly from N-tosyl aziridines in a regio- and stereospecific manner under neutral conditions without the use of any Lewis acid or base has been reported. This methodology is extended to the synthesis of an optically pure cyclic seven-membered disulfide 29. Synthesis of a variety of beta-sulfonamidosulfides involving tandem, multistep reactions in one pot is also reported.
Sureshkumar
Devarajulu
D
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, Karnataka, India.
Gunasundari
Thanikachalam
T
Ganesh
Venkataraman
V
Chandrasekaran
Srinivasan
S
D001388:Aziridines / Q000737:chemistry; D004220:Disulfides / Q000138:chemical synthesis*; D008982:Molybdenum / Q000737:chemistry; D013237:Stereoisomerism; D013440:Sulfides / Q000138:chemical synthesis*; D013449:Sulfonamides / Q000138:chemical synthesis*; D013455:Sulfur / Q000737:chemistry
D001388:Aziridines; D004220:Disulfides; D013440:Sulfides; D013449:Sulfonamides; D013455:Sulfur; D008982:Molybdenum; C020809:tetrathiomolybdate