4.4 Article

Enantioselective Synthesis of Chromanes by Iridium-Catalyzed Asymmetric Hydrogenation of 4H-Chromenes

Journal

SYNLETT
Volume -, Issue 20, Pages 3167-3171

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0028-1087359

Keywords

asymmetric hydrogenation; iridium; P,N-ligands; flavanes; chromanes

Funding

  1. Spanish Ministerio de Educacion, Ciencia y Deporte (MECD)
  2. Fundacion Espanola para la Ciencia y la Tecnologia (FECYT)
  3. Swiss National Science Foundation
  4. Federal Commission for Technology and Innovation (KTI)

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Iridium complexes of chiral oxazoline-based P,N-ligands proved to be efficient catalysts for the enantioselective hydrogenation of 2-aryl- and 2-alkyl-4H-chromenes. The best results were obtained with a ligand derived from threonine (ThrePHOX), which induced ee values of 95% to >99% in the hydrogenation of 2-methyl-, 2-cyclohexyl- and various 2-aryl-substituted chromenes.

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