title: A formal [4 + 4] complementary ambiphile pairing reaction: a new cyclization pathway for ortho-quinone methides.
abstract: A formal, one-pot [4 + 4] cyclization pathway for the generation of eight-membered sultams via in situ generation of an ortho-quinone methide (o-QM) is reported. The pairing of ambiphilic synthons in a complementary fashion is examined whereby o-fluorobenzenesulfonamides are merged with in situ generated o-QM in a formal [4 + 4] cyclization pathway to afford 5,2,1-dibenzooxathiazocine-2,2-dioxide scaffolds under microwave (mW) conditions. The method reported represents the first use of an o-QM in a formal hetero [4 + 4] cyclization.
authors.affiliation: Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, USA.
authors.forename: Thiwanka B
authors.initials: TB
authors.lastname: Samarakoon
authors.forename: Moon Y
authors.initials: MY
authors.lastname: Hur
authors.forename: Ryan D
authors.initials: RD
authors.lastname: Kurtz
authors.forename: Paul R
authors.initials: PR
authors.lastname: Hanson
mesh_terms: D018360:Crystallography, X-Ray; D003500:Cyclization; D045563:Indolequinones / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D045563:Indolequinones; C068040:quinone methide
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