Modular, One-Pot, Sequential Aziridine Ring Opening鈥揝NAr Strategy to 7-, 10-, and 11-Membered Benzo-Fused Sultams

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• 作者：Joanna K. Loh ; Naeem Asad ; Thiwanka B. Samarakoon ; Paul R. Hanson
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：October 16, 2015
• 年：2015
• 卷：80
• 期：20
• 页码：9926-9941
• 全文大小：905K
• ISSN：1520-6904

文摘

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.