REGIOCONTROL AND STEREOSELECTIVITY IN TUNGSTEN-BIPYRIDINE CATALYZED ALLYLIC ALKYLATION

J LEHMANN, GC LLOYDJONES, Guy Lloyd-Jones

Research output: Contribution to journalArticlepeer-review

Abstract

Tungsten-bipyridine complexes, generated in situ, catalyse the allylic alkylation of isocinnamyl methyl carbonate by dimethyl sodiomalonate [NaCH(CO2CH3)(2)] with complete syn-stereoselectivity. When para substituted aryl-allyl methyl carbonates are employed, the regioselectivity correlates with Swain-Lupton parameters. Cross-over experiments demonstrate that the reactions do not procede via the conventional [M(0)] --> [M(II) allyl](+) --> [M(0) allyl-Nu] catalytic cycle.

Original languageEnglish
Pages (from-to)8863-8874
Number of pages12
JournalTetrahedron
Volume51
Issue number32
Publication statusPublished - 7 Aug 1995

Keywords

  • COMPLEXES
  • REGIOCHEMISTRY
  • SUBSTITUTION
  • SELECTIVITY
  • REACTIVITY
  • RESONANCE
  • LIGANDS
  • FIELD

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