Abstract
The Pd-catalyzed TBHP-mediated Wacker-type oxidation of internal alkenes is reported. The reaction uses 2-(4,5-dihydro-2-oxazolyl)quinoline (Quinox) as ligand and TBHP(aq) as oxidant to deliver single ketone constitutional isomer products in a predictable fashion from electronically biased olefins. This methodology is showcased through its application on an advanced intermediate in the total synthesis of the antimalarial drug artemisinin.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Alkenes / chemistry*
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Artemisinins / chemical synthesis*
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Artemisinins / chemistry
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Catalysis
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Ketones / chemical synthesis
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Ketones / chemistry*
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Ligands
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Molecular Structure
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Organometallic Compounds / chemistry*
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Oxazoles / chemistry*
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Oxidation-Reduction
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Palladium / chemistry*
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Quinolines / chemistry*
Substances
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2-(4,5-dihydro-2-oxazolyl)quinoline
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Alkenes
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Artemisinins
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Ketones
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Ligands
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Organometallic Compounds
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Oxazoles
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Quinolines
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Palladium
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artemisinin