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Gold(I) Catalyzed Dearomative Claisen Rearrangement of Allyl, Allenyl Methyl, and Propargyl Aryl Ethers
Organic Letters ( IF 5.2 ) Pub Date : 2017-11-07 00:00:00 , DOI: 10.1021/acs.orglett.7b03306
Michael T. Peruzzi 1 , Stephen J. Lee 2 , Michel R. Gagné 1
Affiliation  

Claisen rearrangements of allyl aryl ethers to generate enones bearing all carbon quaternary centers are accelerated by Ph3PAuNTf2 under mild conditions in good yields. Multiple C–C bond containing variants of the allyl fragment are viable, including alkylidenecyclopropanes, allenes, and alkynes, which generate all-carbon stereogenic centers substituted with vinyl cyclopropanes, 1,3-butadienyl, and allenyl substituents, respectively, for subsequent synthetic manipulation. With allyl phenyl ethers, the product of the [3,3] rearrangements can be trapped by a tandem [4 + 2] cycloaddition to generate complex molecular scaffolds from readily available, achiral starting materials.

中文翻译:

金(I)催化的烯丙基,烯丙基甲基和炔丙基芳基醚的脱芳香性克莱森重排

Ph 3 PAuNTf 2在温和的条件下以高收率促进了烯丙基芳基醚的克莱森重排以生成带有所有碳四元中心的烯酮。包含多个烯丙基片段的C–C键的变体是可行的,包括亚烷基环丙烷,丙二烯和炔烃,它们生成分别被乙烯基环丙烷,1,3-丁二烯基和烯基取代基取代的全碳立构中心,用于后续的合成操作。对于烯丙基苯基醚,可以通过串联[4 + 2]环加成法捕获[3,3]重排的产物,以从易于获得的非手性原料中生成复杂的分子支架。
更新日期:2017-11-07
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