Component match in rhodium catalyzed three-component reactions of ethyl diazoacetate, H2O and aryl imines: a highly diastereoselective one-step synthesis of beta-aryl isoserine derivatives

Org Biomol Chem. 2009 Dec 7;7(23):5028-33. doi: 10.1039/b915013g. Epub 2009 Oct 12.

Abstract

Water and ethyl diazoacetate were found to be matched components for generating highly reactive nucleophilic oxonium ylide in the presence of a dirhodium acetate catalyst. Simultaneous trapping of the oxonium ylide intermediate with aryl imines gave beta-aryl isoserine derivatives with high diastereoselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Crystallography, X-Ray
  • Diazonium Compounds / chemistry*
  • Imines / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Rhodium / chemistry*
  • Serine / analogs & derivatives*
  • Serine / chemical synthesis
  • Serine / chemistry
  • Stereoisomerism
  • Water / chemistry*

Substances

  • Diazonium Compounds
  • Imines
  • Organometallic Compounds
  • Water
  • Serine
  • isoserine
  • Rhodium
  • diazoacetic ester