4.7 Article

Rapid assembly of cyclopentene spiroisoindolinones via a rhodium-catalysed redox-neutral cascade reaction

Journal

CHEMICAL COMMUNICATIONS
Volume 55, Issue 2, Pages 163-166

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c8cc08081j

Keywords

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Funding

  1. Ministry of Science and Technology of China [2016YFE0132600]
  2. Science and Technology of Universities in Henan Province [16HASTIT007]
  3. Zhengzhou University

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An unprecedented strategy of a rhodium-catalysed redox-neutral cascade reaction starting from benzamides and cyclopropenones via addition of a C-H bond into a polar carbonyl group for the rapid assembly of cyclopentene spiroisoindolinones has been developed. Water was produced as the sole by-product. Metal migration and abstraction of a H-atom from the arylcyclopropenone's aromatic ring are the key steps in building the spirocycle. Two C-C bonds, one C-N bond and an N-substituted quaternary carbon center were formed sequentially in a one pot manner.

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