三氟乙酰基原位生成的 3-氟吲哚啉-2-酮衍生的叔烯醇盐与 Morita-Baylis-Hillman 碳酸酯的 Chemoselective S2' 烯丙基化反应。
Chemoselective S2' Allylations of Detrifluoroacetylatively In Situ Generated 3-Fluoroindolin-2-one-Derived Tertiary Enolates with Morita-Baylis-Hillman Carbonates.
机构信息
School of Chemistry and Chemical Engineering, State Key laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Nanjing University , Nanjing 210093, China.
Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU , Paseo Manuel Lardizábal 3, San Sebastián 20018, Spain.
出版信息
J Org Chem. 2017 Dec 15;82(24):13663-13670. doi: 10.1021/acs.joc.7b02409. Epub 2017 Dec 6.
The first example of the S2' reaction type of the detrifluoroacetylatively in situ generated tertiary fluoro-enolates in the uncatalyzed reactions with Morita-Baylis-Hillman derivatives has been described. The S2' substitution takes place in a highly chemoselective manner as no corresponding S2 products were observed in the reaction mixtures. Due to the excellent stereochemical outcome, the reactions seem to have an apparent synthetic value for the preparation of structurally new fluorinated oxindoles.
首次描述了在无催化剂条件下，通过 Morita-Baylis-Hillman 衍生物原位生成的三氟烯醇盐的 S2'反应类型的脱三氟乙酰基反应。S2'取代反应具有高度的化学选择性，因为在反应混合物中没有观察到相应的 S2 产物。由于反应具有优异的立体化学结果，因此这些反应似乎在制备结构新颖的氟化氧吲哚方面具有明显的合成价值。
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