DABCO-catalyzed regioselective cyclization reactions of β,γ-unsaturated α-ketophosphonates or β,γ-unsaturated α-ketoesters with allenic esters

Org Biomol Chem. 2012 Jan 7;10(1):171-80. doi: 10.1039/c1ob06507f. Epub 2011 Nov 17.

Abstract

Highly efficient DABCO-catalyzed [4 + 2] cycloaddition of β,γ-unsaturated α-ketophosphonates or β,γ-unsaturated α-ketoesters with allenic esters gives the corresponding highly functionalized tetrahydropyran and dihydropyran derivatives in good to excellent yields and moderate to good regioselectivities under mild conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Esters
  • Magnetic Resonance Spectroscopy
  • Organophosphonates / chemistry*
  • Piperazines / chemistry*
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Esters
  • Organophosphonates
  • Piperazines
  • triethylenediamine