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Wacker-type oxidation of internal alkenes using Pd(Quinox) and TBHP.

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.

SUBMITTER: DeLuca RJ

PROVIDER: S-EPMC3615722 | biostudies-literature | 2013 Feb

REPOSITORIES: biostudies-literature

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Wacker-type oxidation of internal alkenes using Pd(Quinox) and TBHP.

DeLuca Ryan J RJ Edwards Jennifer L JL Steffens Laura D LD Michel Brian W BW Qiao Xiaoxiao X Zhu Chunyin C Cook Silas P SP Sigman Matthew S MS

The Journal of organic chemistry 20130206 4

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. ...[more]

PMID: 23363387

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