4.5 Article

Axially Chiral Aryl-Alkene-Indole Framework: A Nascent Member of the Atropisomeric Family and Its Catalytic Asymmetric Construction

期刊

CHINESE JOURNAL OF CHEMISTRY
卷 38, 期 6, 页码 543-552

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.202000131

关键词

Atropisomerism; Asymmetric synthesis; Asymmetric catalysis; Chirality

资金

  1. NSFC [21772069, 21831007]
  2. Six Kinds of Talents Project of Jiangsu Province [SWYY-025]

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i Summary of main observation and conclusion A new class of axially chiral aryl-alkene-indole frameworks have been designed, and the first catalytic asymmetric construction of such scaffolds has been established by the strategy of organocatalytic (Z/E)-selective and enantioselective (4+3) cyclization of 3-alkynyl-2-indolylmethanols with 2-naphthols or phenols (all >95 : 5 E/Z, up to 98% yield, 97% ee). This reaction also represents the first catalytic asymmetric construction of axially chiral alkene-heteroaryl scaffolds, which will add a new member to the atropisomeric family. This approach has not only confronted the great challenges in constructing axially chiral alkene-heteroaryl scaffolds but also provided a powerful strategy for the enantioselective construction of axially chiral aryl-alkene-indole frameworks.

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