title: Modular, One-Pot, Sequential Aziridine Ring Opening-S(N)Ar Strategy to 7-, 10-, and 11-Membered Benzo-Fused Sultams.
abstract: The generation of common and stereochemically rich medium-sized benzo-fused sultams via complementary pairing of heretofore-unknown (o-fluoroaryl)sulfonyl aziridine building blocks with an array of amino alcohols/amines in a modular one-pot, sequential protocol using an aziridine ring opening and intramolecular nucleophilic aromatic substitution is reported. The strategy employs a variety of amino alcohols/amines and proceeds with 6 + 4/6 + 5 and 6 + 1 cycloetherification pathways in a highly chemo- and regioselective fashion to obtain skeletally and structurally diverse, polycyclic, 10- to 11- and 7-membered benzo-fused sultams for broad-scale screening.
authors.affiliation: Department of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, United States.|Center for Chemical Methodologies and Library Development (KU-CMLD), Delbert M. Shankel Structural Biology Center, The University of Kansas , 2034 Becker Drive, Lawrence, Kansas 66047, United States.
authors.forename: Joanna K
authors.initials: JK
authors.lastname: Loh
authors.affiliation: Department of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, United States.|Center for Chemical Methodologies and Library Development (KU-CMLD), Delbert M. Shankel Structural Biology Center, The University of Kansas , 2034 Becker Drive, Lawrence, Kansas 66047, United States.
authors.forename: Naeem
authors.initials: N
authors.lastname: Asad
authors.affiliation: Department of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, United States.|Center for Chemical Methodologies and Library Development (KU-CMLD), Delbert M. Shankel Structural Biology Center, The University of Kansas , 2034 Becker Drive, Lawrence, Kansas 66047, United States.
authors.forename: Thiwanka B
authors.initials: TB
authors.lastname: Samarakoon
authors.affiliation: Department of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, United States.|Center for Chemical Methodologies and Library Development (KU-CMLD), Delbert M. Shankel Structural Biology Center, The University of Kansas , 2034 Becker Drive, Lawrence, Kansas 66047, United States.
authors.forename: Paul R
authors.initials: PR
authors.lastname: Hanson
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D009282:Naphthalenesulfonates / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001388:Aziridines; D009282:Naphthalenesulfonates; C033132:aziridine; C016768:naphthosultone