Asymmetric Aldol/Vinylogous Aldol/Cyclization Reaction Using Phosphine Oxide Catalysts

Chem Pharm Bull (Tokyo). 2017;65(10):989-993. doi: 10.1248/cpb.c17-00540.

Abstract

Chiral phosphine oxide sequentially activates silicon tetrachloride and trichlorosilyl enol ethers to facilitate asymmetric aldol/vinylogous aldol reaction of 4-methoxy-3-penten-2-one and conjugated aldehydes in a highly enantioselective fashion, and the subsequent cyclization produced optically active 2,6-disubstituted 2,3-dihydro-4-pyranones bearing stereogenic centers at a remote position in a single operation.

Keywords: asymmetric catalysis; phosphine oxide; pyranone; remote-control; tandem reaction.

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Chlorides / chemistry
  • Crystallography, X-Ray
  • Cycloaddition Reaction
  • Molecular Conformation
  • Oxides / chemistry
  • Phosphines / chemistry*
  • Silicon Compounds / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Chlorides
  • Oxides
  • Phosphines
  • Silicon Compounds
  • 3-hydroxybutanal
  • silicon tetrachloride
  • phosphine