Open AccessModular, One-Pot, Sequential Aziridine Ring Opening–SNAr Strategy to 7-, 10-, and 11-Membered Benzo-Fused Sultams
Author(s) -
Joanna K. Loh,
Naeem Asad,
Thiwanka Bandara Samarakoon,
Paul R. Hanson
Publication year - 2015
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.5b01429
Subject(s) - aziridine , chemistry , regioselectivity , intramolecular force , ring (chemistry) , stereochemistry , nucleophilic aromatic substitution , nucleophilic substitution , combinatorial chemistry , organic chemistry , catalysis
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.