Efficient asymmetric oxidation of sulfides and kinetic resolution of sulfoxides catalyzed by a vanadium-salan system.
The asymmetric oxidation of sulfides to chiral sulfoxides with hydrogen peroxide in good yield and high enantioselectivity has been catalyzed very effectively by chiral vanadium-salan [N,N'-alkyl bis(salicylamine)] complex. The salan ligand shows results superior in terms of reactivity and enantioselectivity to those of salen [N,N'-alkylene bis(salicylideneimine)] analogue, and provides the sulfoxide with opposite configuration. The high enantioselectivity of this reaction is the direct result of the asymmetric oxidation. The efficient kinetic resolution of racemic sulfoxides catalyzed by the vanadium-salan system is also described.
Sun
Jiangtao
J
School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, China.
Zhu
Chengjian
C
Dai
Zhenya
Z
Yang
Minghua
M
Pan
Yi
Y
Hu
Hongwen
H
D002384:Catalysis; D007700:Kinetics; D008024:Ligands; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D012459:Salicylates / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry*; D013454:Sulfoxides / Q000138:chemical synthesis / Q000737:chemistry*; D014639:Vanadium / Q000737:chemistry*
D008024:Ligands; D009942:Organometallic Compounds; D012459:Salicylates; D013440:Sulfides; D013454:Sulfoxides; D014639:Vanadium