Journal of the American Chemical Society p. 8188 - 8193 (1984)
Update date:2022-08-06
Topics:
Pitchen, P.
Dunach, E.
Deshmukh, M. N.
Kagan, H. B.
The Sharpless reagent for asymmetric epoxidation was modified by addition of 1 mol equiv of H2O to give a new homogenous reagent (Ti(O-i-Pr)4/diethyl tartrate/H2O/t-BuOOH = 1:2:1:1).This reagent cleanly oxidizes prochiral functionalized sulfides into optically active sulfoxides.The observed ee mainly ranged between 75 and 90percent for alkyl aryl sulfoxides and 50-71percent for dialkyl sulfoxides.A strong temperature dependence on ee was also observed in the asymmetric oxidation of methyl p-tolyl sulfoxide.
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