Organic sulfur chemistry. Part XXII. The reaction of sulfinate esters with Grignard and organocopper lithium reagents. A useful route to chiral sulfoxides

DN Harpp, SM Vines, JP Montillier…

Index: Harpp,D.N. et al. Journal of Organic Chemistry, 1976 , vol. 41, # 25 p. 3987 - 3992

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Citation Number: 59

Abstract

The reaction of sulfinate esters with various Grignard reagents was found to give a complex mixture of sulfoxide and sulfides, The use of organocopper lithium reagents in place of the Grignard effects the conversion of sulfinate esters to sulfoxides in higher yields and cleaner product mixtures.(-)-Menthyl (-)-(SI-p-toluenesulfinate and (-)-menthyl (-)-(S)- benzenesulfinate were treated with organocopper lithium reagents. The reactions were ...