Directive and shielding effects of the trimethylsilyl group. Unprecedented β-selectivity in the reaction of α, β-epoxyalkylsilanes with hindered α-sulphonyl anions

P Jankowski, S Marczak, M Masnyk…

Index: Jankowski, Pawel; Marczak, Stanislaw; Masnyk, Marek; Wicha, Jerzy Journal of the Chemical Society, Chemical Communications, 1991 , # 5 p. 297 - 298

Full Text: HTML

Citation Number: 0

Abstract

It is well documented that the reaction of (a7(3-epoxyalkyl)- silanes with many nucleophiles occurs regioselectively with addition of the nucelophile at the a-position. 1 No exception to the a-attack rule had been recorded? (to the best of our knowledge) until Schaumann and Kirsching3 recently repor- ted that the reaction of lithiated allylsilanes with some (a,p-epoxyalky1)silanes affords the products of addition in the a-position, accompanied by various amounts (up to 25%) of ...