Chinese Journal of Organic Chemistry >
Oxidation Kinetics Resolution of Racemic Aromatic Sulfoxides by Chiral Porphyrin-Inspired N4 Ligand with Manganese Complex
Received date: 2018-05-16
Revised date: 2018-06-19
Online published: 2018-07-05
Supported by
Project supported by the National Natural Science Foundation of China (No. 21403100) and the Education Research Program of the Education Department of Liaoning Province (No. L2014421).
Oxidative kinetics resolution of racemic aromatic sulfoxide was studied by using chiral porphyrin-inspired N4 ligands and manganese in situ complex as catalyst, environment-friendly H2O2 as oxidant and adamantanecarboxylic acid as additive. The arylalkyl and arylbenzyl sulfoxide substrates were extended by this catalytic system. A maximum yield of chiral sulfoxide was 40% and the enantioselectivity was 100%. In the meantime, the yield of sulfone a further oxidation products of sulfoxide, was up to 72%. It was found that the catalytic oxidation system is more prone to electron-rich sulfoxide through the competition experiment between electron-rich sulfoxide and electron-deficient sulfoxide substrates. In addition, the success of gram-scale oxidation kinetic resolution also shows that this method has a certain practical value in methodology.
Key words： ligand N4; manganese; oxidative kinetic resolution; aromatic sulfoxides; sulfone
Yang Jinchuang, Li Guosong, Lü Chengwei, An Yue, Gao Shuang . Oxidation Kinetics Resolution of Racemic Aromatic Sulfoxides by Chiral Porphyrin-Inspired N4 Ligand with Manganese Complex[J]. Chinese Journal of Organic Chemistry, 2018 , 38(11) : 3070 -3077 . DOI: 10.6023/cjoc201805034
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