Construction of Azabicyclo[6.4.0]dodecatrienes Based on Rhodium(I)-Catalyzed Intramolecular [6+2] Cycloaddition between Azetidine, Allene, and Alkynes

Chem Pharm Bull (Tokyo). 2016;64(7):805-10. doi: 10.1248/cpb.c16-00178.

Abstract

Treatment of the allenylazetidine-alkynes with a catalytic amount of [RhCl(CO)dppp]2 (dppp: 1,3-bis(diphenylphosphino)propane) effected the intramolecular hetero-[6+2]-type ring-closing reaction via the C-C bond cleavage of the azetidine ring to produce azabicyclo[6.4.0]dodecatriene derivatives in good to excellent yields. The formation of the oxa analogue could also be achieved.

MeSH terms

  • Alkadienes / chemistry*
  • Alkynes / chemistry*
  • Azabicyclo Compounds / chemical synthesis*
  • Azabicyclo Compounds / chemistry
  • Azetidines / chemistry*
  • Catalysis
  • Cyclization
  • Molecular Structure
  • Rhodium / chemistry*

Substances

  • Alkadienes
  • Alkynes
  • Azabicyclo Compounds
  • Azetidines
  • azetidine
  • propadiene
  • Rhodium