Control of chemo-and stereoselectivity in the reactions of organocuprates with. alpha.-oxoketene dithioacetals

RK Dieter, LA Silks III, JA Fishpaugh…

Index: Dieter,R.K.; Silks,L.A.; Fishpaugh,J.R. Journal of the American Chemical Society, 1985 , vol. 107, p. 4679

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Citation Number: 100

Abstract

Abstract: n-Oxoketene dithioacetals can be induced to undergo a selective substitution reaction with organocopper reagents to afford@-alkylthio-a,@-enones. The effect of substrate structure, transferable copper ligand, copper reagent, and solvent upon the chemo- and stereoselectivity of the reaction was examined. Cyclic and acyclic substrates afforded the E@-alkylthio-a,@-enones in good to excellent yields with generally high ...