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Synthesis of gem ‐Difluorinated Spiro‐γ‐lactam Oxindoles by Visible‐Light‐Induced Consecutive Difluoromethylative Dearomatization, Hydroxylation, and Oxidation
Author(s) -
Wang Qiang,
Qu Yi,
Xia Qing,
Song Hongjian,
Song Haibin,
Liu Yuxiu,
Wang Qingmin
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201802141
Subject(s) - hydroxylation , lactam , chemistry , beta lactam , visible spectrum , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , antibiotics , materials science , biochemistry , optoelectronics , enzyme
Described herein is a protocol for visible‐light‐induced consecutive synthesis of gem ‐difluorinated spiro‐γ‐lactam oxindoles under mild conditions by means of a process involving sequential radical difluoromethylative dearomatization, hydroxylation, and oxidation. The protocol features high chemo‐ and regioselectivity, good functional group tolerance, and easy scalability. Several of the functionalized spirooxindole products showed good fungicidal activity, suggesting that they have potential agrochemical applications.