Palladium-catalyzed asymmetric allylic alkylation of electron-deficient pyrroles with meso electrophiles

Org Lett. 2012 May 4;14(9):2254-7. doi: 10.1021/ol3006584. Epub 2012 Apr 16.

Abstract

Pyrroles can serve as competent nucleophiles with meso electrophiles in the Pd-catalyzed asymmetric allylic alkylation. The products from this transformation were obtained as a single regio- and diastereomer in high yield and enantiopurity. A nitropyrrole-containing nucleoside analogue was synthesized in seven steps to demonstrate the synthetic utility of this transformation.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkylation
  • Allyl Compounds / chemistry*
  • Catalysis
  • Molecular Structure
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Palladium / chemistry*
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry*
  • Stereoisomerism

Substances

  • Allyl Compounds
  • Nucleosides
  • Pyrroles
  • Palladium