Bifunctionalized Allenes. Part XVI. Synthesis of 3-Phosphoryl-2,5-dihydrofurans by Coinage Metal-Catalyzed Cyclo-isomerization of Phosphorylated α-Hydroxyallenes

Molecules. 2015 Apr 21;20(4):7263-75. doi: 10.3390/molecules20047263.

Abstract

Phosphorylated α-hydroxyallenes 1 and 2 were smoothly converted into the corresponding 2,5-dihydrofurans 3 and 4 in an 5-endo-trig cycloisomerization reaction by using 5 mol % of coinage metal salts as catalyst. Experimental conditions such as the type of the solvent, the reaction temperature, the mol % and the type of the catalyst were optimized. This mild and efficient cyclization method can be applied to dimethyl 1-hydroxyalkyl-alka-1,2-dienephosphonates 1 and 2-diphenylphosphinoyl-2,3-dien-1-ols 2a-c and 3-diphenylphosphinoyl-3,4-dien-2-ols 2d,e, furnishing 3-phosphorylated 2,5-dihydrofurans 3 and 4 in very good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkadienes / chemical synthesis
  • Alkadienes / chemistry*
  • Chemistry Techniques, Synthetic
  • Cyclization
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Isomerism
  • Molecular Structure
  • Phosphorylation

Substances

  • Alkadienes
  • Furans