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Catalytic Asymmetric Synthesis of 3-Hydroxy-3-trifluoromethyl Benzofuranones via Tandem Friedel-Crafts/Lactonization Reaction
Alternative Title不对称催化串联付-克/内酯化反应合成3-羟基-3-三氟甲基苯并呋喃酮
Ren H(任海); Wang P(王盼); Wang LJ(王丽佳); Tang Y(唐勇)
2015
Source PublicationOrg. Lett.
Volume17Issue:19Pages:4886-4889
AbstractA highly enantioselective and regioselective chiral Lewis acid catalyzed tandem Friedel-Crafts/lactonization reaction is reported, providing direct access to plenty of 3-hydroxy-3-trifluoromethyl benzofuran-2-ones in up to 94% yields with up to >99% ee. Mechanistic study reveals that the interactions between the phenolic hydroxyl group and trifluoropyruvate are the most likely contributing factor to the high enantio- and regioselectivity. Optically pure (-)-BHFF can be obtained in gram-scale with 0.05 mol % catalyst, demonstrating the potentially utility of this method in medicinal chemistry.
Subtype论文
Subject Area金属有机化学
DOI10.1021/acs.orglett.5b02440
URL查看原文
Indexed BySCI
Language英语
WOS IDWOS:000362384700060
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Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/39642
Collection金属有机化学国家重点实验室
Corresponding AuthorWang LJ(王丽佳); Tang Y(唐勇)
Affiliation中科院上海有机化学研究所, 金属有机化学国家重点实验室
Recommended Citation
GB/T 7714
Ren H,Wang P,Wang LJ,et al. Catalytic Asymmetric Synthesis of 3-Hydroxy-3-trifluoromethyl Benzofuranones via Tandem Friedel-Crafts/Lactonization Reaction[J]. Org. Lett.,2015,17(19):4886-4889.
APA 任海,王盼,王丽佳,&唐勇.(2015).Catalytic Asymmetric Synthesis of 3-Hydroxy-3-trifluoromethyl Benzofuranones via Tandem Friedel-Crafts/Lactonization Reaction.Org. Lett.,17(19),4886-4889.
MLA 任海,et al."Catalytic Asymmetric Synthesis of 3-Hydroxy-3-trifluoromethyl Benzofuranones via Tandem Friedel-Crafts/Lactonization Reaction".Org. Lett. 17.19(2015):4886-4889.
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