Synthesis of functionalized chromans by PnBu3-catalyzed reactions of salicylaldimines and salicylaldehydes with allenic ester

Org Lett. 2010 Dec 17;12(24):5664-7. doi: 10.1021/ol102461c. Epub 2010 Nov 11.

Abstract

P(n)Bu(3)-catalyzed cyclization reactions of salicylaldimines and salicylaldehydes with ethyl 2,3-butadienoate gave the corresponding functionalized chromans in moderate to good yields in THF under mild conditions. The new reaction provides a new method for the synthesis of biologically active chroman products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Alkadienes / chemistry*
  • Catalysis
  • Chromans / chemistry*
  • Crystallography, X-Ray
  • Esters / chemistry*
  • Imines / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Phosphines / chemistry*

Substances

  • Aldehydes
  • Alkadienes
  • Chromans
  • Esters
  • Imines
  • Phosphines
  • tri-n-butylphosphine
  • salicylaldehyde
  • propadiene