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Enantioselective Friedel–Crafts C2-alkylation of 3-substituted indoles with trifluoropyruvates and cyclic N-sulfonyl α-ketiminoesters†
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2017-12-13 00:00:00 , DOI: 10.1039/c7qo01014a
Bing-Bing Huang 1, 2, 3, 4 , Liang Wu 1, 2, 3, 4 , Ren-Rong Liu 1, 2, 3, 4 , Ling-Ling Xing 1, 2, 3, 4 , Ren-Xiao Liang 1, 2, 3, 4 , Yi-Xia Jia 1, 2, 3, 4
Affiliation  

Enantioselective Friedel–Crafts C2-alkylation reactions of 3-substituted indoles with trifluoropyruvates and cyclic N-sulfonyl α-ketiminoesters were developed by using the complexes of Cu(OTf)2 or Zn(OTf)2 with chiral bisoxazoline ligands. A range of chiral indole-containing trifluoromethylated α-hydroxyesters and cyclic α-aminoesters bearing quaternary stereogenic centers were afforded in good yields and excellent enantioselectivities (up to 99% ee) under mild conditions.

中文翻译:

对映选择性的 Friedel–Crafts将三取代的吲哚与三氟丙酮酸酯和环状N-磺酰基α-酮亚氨基酸酯进行C2-烷基化反应

通过使用Cu(OTf)2或Zn(OTf)2与手性双恶唑啉配体的配合物,开发了3-取代的吲哚与三氟丙酮酸和环状N-磺酰基α-酮亚氨基酸酯的对映选择性Friedel-Crafts C2-烷基化反应。在温和条件下,以良好的收率和优异的对映选择性(高达99%ee)提供了一系列带有季立体异构中心的手性含吲哚的三氟甲基化α-羟基酯和环状α-氨基酯。
更新日期:2017-12-13
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