Ring-opening of 2, 3-epoxy-1-propanol with R 3 Al: Unprecedented regiochemical switching simply achieved by changing alkyl substituents of aluminium reagent

…, P Horeglad, E Tratkiewicz, I Justyniak, Z Ochal

Index: Lewinski, Janusz; Horeglad, Pawel; Tratkiewicz, Ewa; Justyniak, Iwona; Ochal, Zbigniew Journal of Organometallic Chemistry, 2005 , vol. 690, # 16 p. 3697 - 3699

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Citation Number: 5

Abstract

Several control experiments were designed to optimize the reaction of 2, 3-epoxy-1- propanol with R3Al (R= Me, Et or iBu) and to probe for the nature of aluminium-bound alkyl groups that influence the reactivity and selectivity. The reported studies revealed that the Et3Al mediated reaction leads to the C-2 product in contrast to the well-known C-3 substitution promoted by Me3Al.