Formal [4+3] epoxide cascade reaction via a complementary ambiphilic pairing strategy.
A formal [4+3] epoxide cascade protocol utilizing ambiphilic sulfonamides and a variety of epoxides (masked ambiphiles) has been developed for the generation of benzothiaoxazepine-1,1'-dioxides and oxathiazepine-1,1'-dioxides. This protocol combines an epoxide ring-opening with either an S(N)Ar or oxa-Michael cyclization pathway.
Rolfe
Alan
A
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA.
Samarakoon
Thiwanka B
TB
Hanson
Paul R
PR
D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*; D013841:Thiazepines / Q000138:chemical synthesis* / Q000737:chemistry
D004852:Epoxy Compounds; D013449:Sulfonamides; D013841:Thiazepines