New pinene-derived pyridines as bidentate chiral ligands

A.V. Malkov, A.J.P. Stewart-Liddon, F. Teply, L. Kobr, K.W. Muir, David Haigh, P. Kocovsky

Research output: Contribution to journalArticlepeer-review

42 Citations (Scopus)

Abstract

A synthesis of new bidentate pyridines has been developed, starting from ?-pinene. A copper complex of the pyridine-oxazoline ligands catalyzes asym. allylic oxidn. of cyclic olefins with good conversion rates and acceptable enantioselectivity (?67% ee). The imidazolium salt I has been identified as a precursor of the N,N'-unsym. N-heterocyclic carbene ligand, which upon complexation with palladium, catalyzed the intramol. amide enolate ?-arylation leading to oxindole in excellent yield but with low enantioselectivity.
Original languageEnglish
Pages (from-to)4011-4025
Number of pages15
JournalTetrahedron
Volume64
Issue number18
DOIs
Publication statusPublished - 28 Apr 2008

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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