Wacker-Type Oxidation of Internal Alkenes using Pd(Quinox) and TBHP
The Journal of Organic Chemistry2013Vol. 78(4), pp. 1682–1686
Citations Over TimeTop 10% of 2013 papers
Ryan J. DeLuca, Jennifer L. Edwards, Laura D. Steffens, Brian W. Michel, Xiaoxiao Qiao, Chunyin Zhu, Silas P. Cook, Matthew S. Sigman
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.
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