Bifunctional ferrocene-based squaramide-phosphine as an organocatalyst for highly enantioselective intramolecular Morita-Baylis-Hillman reaction

Org Biomol Chem. 2014 Apr 21;12(15):2423-6. doi: 10.1039/c4ob00137k.

Abstract

This work demonstrates that, in accord with metal catalysis, ferrocene could be an excellent scaffold for organocatalysts. The simple and easily accessible bifunctional ferrocene-based squaramide-phosphine shows high enantioselectivity in the intramolecular Morita-Baylis-Hillman reaction of 7-aryl-7-oxo-5-heptenals, giving a variety of 2-aroyl-2-cyclohexenols in up to 96% ee.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Catalysis
  • Ferrous Compounds / chemistry*
  • Metallocenes
  • Phosphines / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Amides
  • Ferrous Compounds
  • Metallocenes
  • Phosphines
  • phosphine
  • ferrocene