New pinene-derived pyridines as bidentate chiral ligands |
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| Authors: | Andrei V Malkov Angus JP Stewart-Liddon Filip Teplý Lukáš Kobr Kenneth W Muir Pavel Ko?ovský |
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| Institution: | a Department of Chemistry, WestChem, Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, Scotland, UK
b Department of Medicinal Chemistry, Metabolic and Viral Centre of Excellence for Drug Discovery, GlaxoSmithKline Pharmaceuticals, Medicines Research Centre, Stevenage, Hertfordshire SG1 2NY, UK |
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| Abstract: | A synthesis of new bidentate pyridines 8a-d, 9, and 10 has been developed, starting from triflate 14, readily available from β-pinene 11. A copper complex of the pyridine-oxazoline ligands 8a has been found to catalyze asymmetric allylic oxidation of cyclic olefins 36a-c with good conversion rates and acceptable enantioselectivity (≤67% ee). The imidazolium salt 10 has been identified as a precursor of the corresponding N,N′-unsymmetrical N-heterocyclic carbene ligand, whose complex with palladium catalyzed the intramolecular amide enolate α-arylation leading to oxindole 45 in excellent yield but with low enantioselectivity. |
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| Keywords: | Chiral ligands Transition metal catalysis Asymmetric catalysis Pyridine ligands Oxazoline ligands N N&prime -Heterocyclic carbene ligands |
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