Amine-catalyzed enantioselective 1,3-dipolar cycloadditions of aldehydes to C,N-cyclic azomethine imines

Chemistry. 2014 Apr 14;20(16):4559-62. doi: 10.1002/chem.201400333. Epub 2014 Mar 18.

Abstract

Amine-catalyzed enantioselective 1,3-dipolar cycloadditions of aldehydes to C,N-cyclic azomethine imines were developed. The reactions between diversely substituted C,N-cyclic azomethine imines and aldehydes proceeded smoothly in the presence of chiral prolinol silyl ether catalyst and gave the C-1-substituted tetrahydroisoquinolines in a highly stereoselective manner. These tetrahydroisoquinolines could be efficiently transformed to several other useful polycyclic frameworks.

Keywords: asymmetric synthesis; cycloadditions; enamines; heterocycles; tetrahydroisoquinoline.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Amines / chemistry*
  • Azo Compounds / chemistry*
  • Catalysis
  • Cyclization
  • Cycloaddition Reaction
  • Heterocyclic Compounds / chemistry
  • Imines / chemical synthesis
  • Imines / chemistry*
  • Stereoisomerism
  • Tetrahydroisoquinolines / chemical synthesis
  • Tetrahydroisoquinolines / chemistry
  • Thiosemicarbazones / chemistry*

Substances

  • Aldehydes
  • Amines
  • Azo Compounds
  • Heterocyclic Compounds
  • Imines
  • Tetrahydroisoquinolines
  • Thiosemicarbazones
  • azomethine