Synthesis and reactivity of unsymmetrical azomethine imines formed using alkene aminocarbonylation

Org Lett. 2013 Apr 19;15(8):1890-3. doi: 10.1021/ol400542b. Epub 2013 Apr 8.

Abstract

Complex cyclic azomethine imines possessing a β-aminocarbonyl motif can be accessed readily from simple alkenes and hydrazones. This alkene aminocarbonylation approach allows formation of ketone-derived azomethine imines of unprecedented complexity. Since unsymmetrical hydrazones are used, two stereoisomers are formed: the reactivity of chiral derivatives is explored in both intra- and intermolecular systems.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Azo Compounds / chemical synthesis*
  • Azo Compounds / chemistry
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Cyclization
  • Hydrazones / chemistry*
  • Imines / chemical synthesis*
  • Imines / chemistry
  • Ketones / chemical synthesis
  • Ketones / chemistry
  • Molecular Structure
  • Stereoisomerism
  • Thiosemicarbazones / chemical synthesis*
  • Thiosemicarbazones / chemistry

Substances

  • Alkenes
  • Azo Compounds
  • Hydrazones
  • Imines
  • Ketones
  • Thiosemicarbazones
  • azomethine