4.7 Article

Iron-catalysed asymmetric tandem spiro-cyclization using dioxygen in air as the hydrogen acceptor

Journal

CHEMICAL COMMUNICATIONS
Volume 50, Issue 39, Pages 5053-5056

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c4cc01555j

Keywords

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Funding

  1. Advanced Catalytic Transformation program for Carbon Utilization (ACT-C)
  2. JST
  3. Nissan Chemical Industries, Ltd.
  4. International Institute for Carbon-Neutral Energy Research (WPI-I2CNER) from MEXT, Japan
  5. JSPS
  6. Grants-in-Aid for Scientific Research [23245009, 11J03551] Funding Source: KAKEN

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A tandemcombination of ortho-quinone methide (o-QM) formation/Michael addition/asymmetric dearomatization, which is catalysed by an iron-salan complex in air with high enantioselectivity, provides an efficient method for spirocyclic (2H)-dihydrobenzofuran synthesis from 2-naphthols and phenols. The key to the success of the tandem synthesis is the development of aerobic oxidative o-QM formation.

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