期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 68, 期 1, 页码 150-155出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo0205560
关键词
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The mechanism of the oxidation of di-tert-butyl disulfide (1) to the chiral thiosulfinate (2) by H2O2 catalyzed by bis(acetylacetonato)oxovanadium and a chiral Schiff-base ligand (3) has been investigated. Techniques included V-51 NMR spectroscopy, solvent effects on reaction enantioselectivity, and the isolation and full characterization of a 2:1 ligand-to-vanadium catalyst precursor. A model for the dramatic solvent effect on the enantioselectivity of this reaction was developed, based on the identification of a competing nonselective oxidation pathway. From this model, strategies for limiting this competing pathway were developed.
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