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