Isotopic desymmetrisation as a stereochemical probe

GC Lloyd-Jones*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Molecular symmetry can sometimes be a major impediment to the elucidation of stereochemical information. In certain cases, the appropriate placement of a stable isotope (e.g. H-2, C-13 and O-18 can allow isotopic desymmetrisation with only minor perturbations in reactivity relative to the unlabelled compound. Memory effects in palladium-catalysed allylic alkylation and N-chiral proton sponges are two such cases in which isotopic desymmetrisation may be employed with minimal effort and with great effect.

Original languageEnglish
Pages (from-to)161-183
Number of pages23
Journal Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry
Issue number2
Publication statusPublished - Feb 2001

Keywords

  • stable isotopes
  • Pd-allyl complexes
  • proton sponges
  • NMR
  • CATALYZED ALLYLIC ALKYLATION
  • PALLADIUM-MOP COMPLEXES
  • STRONG HYDROGEN-BONDS
  • ASYMMETRIC HYDROSILYLATION
  • KINETIC RESOLUTION
  • 2-AMINO-2'-DIPHENYLPHOSPHINO-1,1'-BINAPHTHYL MAP
  • MOLYBDENUM CATALYSTS
  • ENZYMATIC CATALYSIS
  • SUBSTITUTION
  • LIGANDS

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