4.7 Article

Regio- and enantioselective ring-opening reaction of vinylcyclopropanes with indoles under cooperative catalysis

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ORGANIC CHEMISTRY FRONTIERS
卷 8, 期 2, 页码 -

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ROYAL SOC CHEMISTRY
DOI: 10.1039/d0qo00699h

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资金

  1. National Natural Science Foundation of China [21772069, 21831007]
  2. Six Kinds of Talents Project of Jiangsu Province [SWYY-025]
  3. Undergraduate Students Project of Jiangsu Province
  4. Natural Science Research Project of Jiangsu Higher Education Institutions of China [18KJB150031]
  5. TAPP

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The study established a reaction under the cooperative bimetallic catalysis of iridium and copper catalysts, which yielded indole C3-allylation products with moderate yields (up to 78%) and good enantioselectivities (up to 97:3 er). This reaction not only represents the first catalytic asymmetric ring-opening reaction of vinylcyclopropanes with C3-unsubstituted indoles, but also provides an atom-economic and straightforward method for the synthesis of C3-allylic indoles with high regio- and enantioselectivity.
The title reaction has been established under the cooperative bimetallic catalysis of iridium and copper catalysts, which afforded indole C3-allylation products with branched selectivity in moderate yields (up to 78%) and good enantioselectivities (up to 97 : 3 er). This reaction not only represents the first catalytic asymmetric ring-opening reaction of vinylcyclopropanes with C3-unsubstituted indoles, but also has provided an atom-economic and straightforward method for the synthesis of C3-allylic indoles with high regio- and enantioselectivity.

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