γ-silyl group effect in hydroalumination and carbolithiation of propargylic alcohols

Abstract

(Chemical Equation Presented) Making the right substitution: A remarkable acceleration effect of phenyl-substituted silyl groups in hydroalumination and carbolithiation reactions of propargylic alcohols (see formula) is described. The results show that an aryl silyl group can act not only as a protecting group but also as an activating group of the alkynyl moiety. This work provides an efficient group-selective approach to multifunctionalized alkenes. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.