Expanding insight into asymmetric palladium-catalyzed allylic alkylation of N-heterocyclic molecules and cyclic ketones

Chemistry. 2013 Apr 2;19(14):4414-8. doi: 10.1002/chem.201300030. Epub 2013 Feb 27.

Abstract

Eeny, meeny, miny ... enaminones! Lactams and imides have been shown to consistently provide enantioselectivities substantially higher than other substrate classes previously investigated in the palladium-catalyzed asymmetric decarboxylative allylic alkylation. Several new substrates have been designed to probe the contributions of electronic, steric, and stereoelectronic factors that distinguish the lactam/imide series as superior alkylation substrates (see scheme). These studies culminated in marked improvements on carbocyclic allylic alkylation substrates.

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
  • Catalysis
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Ketones / chemistry
  • Lactams
  • Molecular Structure
  • Oxazoles / chemistry
  • Palladium / chemistry*
  • Phosphines / chemistry

Substances

  • Heterocyclic Compounds
  • Ketones
  • Lactams
  • Oxazoles
  • Phosphines
  • Palladium