An efficient asymmetric oxidation of sulfides to sulfoxides

…, E Dunach, MN Deshmukh, HB Kagan

Index: Pitchen, P.; Dunach, E.; Deshmukh, M. N.; Kagan, H. B. Journal of the American Chemical Society, 1984 , vol. 106, # 26 p. 8188 - 8193

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Citation Number: 627

Abstract

Abstract: The Sharpless reagent for asymmetric epoxidation was modified by addition of 1 mol equiv of H20 to give a new homogeneous reagent (Ti (0-i-Pr),/diethyl tartrate/H20/t- Bu00H= 1: 2: l: 1). This reagent cleanly oxidizes prochiral functionalized sulfides into optically active sulfoxides. The observed ee mainly ranged between 75 and 90% for alkyl aryl sulfoxides and 50-71% for dialkyl sulfoxides. A strong temperature dependence on ee ...