Reversal of. pi.-facial diastereoselection upon electronegative substitution of the substrate and the reagent

AS Cieplak, BD Tait, CR Johnson

Index: Cieplak, Andrzej S.; Tait, Bradley D.; Johnson, Carl R. Journal of the American Chemical Society, 1989 , vol. 111, # 22 p. 8447 - 8462

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Citation Number: 273

Abstract

Abstract: Electronegative substitution at C-3 of cyclohexanone and methylenecyclohexane is found to increase the relative proportion of axial attack in a number of reactions widely differing from the points of view of the transition-state polarization, geometry, and electron deficiency. Reactions examined included alkyllithium additions, oxymercurations, osmylations, and peracid epoxidations. Plots of log k,,/k, vs uI (1.2 values of 0.952, 0.940, ...

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