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

Wacker-type oxidation of internal alkenes using Pd(Quinox) and TBHP.
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DOI:
10.1021/jo302638v
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发表时间:
2013-02-15
期刊:
The Journal of organic chemistry
影响因子:
--
通讯作者:
Sigman MS
Sigman MS
中科院分区:
其他
文献类型:
--
作者:
DeLuca RJ;Edwards JL;Steffens LD;Michel BW;Qiao X;Zhu C;Cook SP;Sigman MS

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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 anti-malarial drug, artemisinin.
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