4.6 Article

Highly enantioselective iron(II)-catalyzed opening reaction of aromatic meso-epoxides with indoles

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 11, Issue 43, Pages 7463-7466

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob41782d

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Funding

  1. Natural Sciences and Engineering Research Council of Canada (NSERC)
  2. Centre in Green Chemistry and Catalysis (CGCC)
  3. Canada Foundation for Innovation (CFI)
  4. Universite Laval
  5. NSERC
  6. Fonds Quebecois de la Recherche Nature et technologies (FQRNT)

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A highly enantioselective method for the catalytic cis-stilbene oxide opening reaction with indole derivatives was developed. The scope of the reaction was studied with a selection of aromatic meso-epoxides and various indoles, and the desired 2-(indol-3-yl)ethanol derivatives were obtained in good to excellent yields with excellent enantioselectivities (from 96 to >99% ee).

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