4.8 Article

Unusual biaryl torsional strain promotes reactivity in Cu-catalyzed Sommelet-Hauser rearrangement

Journal

CHEMICAL SCIENCE
Volume 9, Issue 26, Pages 5850-5854

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c8sc01657g

Keywords

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Funding

  1. NSFC [21622206, 21472179]
  2. 973' project from the MOST of China [2015CB856600]
  3. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
  4. Fundamental Research Funds for the Central Universities [WK2060190086]

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A Cu-catalyzed Sommelet-Hauser dearomatization of dihydrophenanthridine and diazo compounds is reported for the synthesis of spiro-indolines. A spiro-structure with adjacent quaternary and tertiary carbon centers was constructed in one step as a single isomer. Increasing steric hindrance by introducing ortho-substituents dramatically improved substrate reactivity in this transformation.

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