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Volumn , Issue 7, 2003, Pages 1046-1048

Nb(salen)-catalyzed sulfoxidation

Author keywords

Asymmetric catalysis; Niobium; Niobium(salen) complex; Sulfoxidation

Indexed keywords

HYDROGEN PEROXIDE; NIOBIUM; OXIDIZING AGENT; UREA;

EID: 0037561602     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-39321     Document Type: Article
Times cited : (45)

References (24)
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    • note
    • 3(dme) and salen ligand in these ways showed inferior catalytic activity in terms of enantioselectivity (for examples, the oxidation of methyl phenyl sulfides with these Nb-4 complexes at room temperature showed 12-46% ee).
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    • note
    • 3(dme) (2.3 mg, 8.0 μmol) were dissolved in dichloromethane (2 mL) in a glovebox, and the solution was stirred for 2 h at room temperature. After addition of MS 4 Å (ca. 20 mg), the mixture was stirred for another 30 min. The mixture was taken out of the glovebox and cooled to -10°C under nitrogen. To this mixture were added methyl phenyl sulfide (12.0 μL, 0.10 mmol) and urea-hydrogen peroxide adduct (UHP) (10.5 mg, 0.11 mmol) successively, and the mixture was stirred for 2 days at the temperature. The mixture was directly chromatographed on silica gel (hexane-ethyl acetate = 1:1-1:19) to give methyl phenyl sulfoxide (12.4 mg, 88%). The enantiomeric excess of the sulfoxide was determined to be 86% ee by HPLC analysis using chiral stationary phase column (Daicel Chiralcel OD-H, hexane-i-PrOH = 9:1).


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