Pentacoordinate organoaluminum chemistry: Catalytic efficiency of Me3Al in the epoxide cleavage with alkynyllithiums

…, N Kagoshima, H Ichikawa, K Maruoka

Index: Ooi; Kagoshima; Ichikawa; Maruoka Journal of the American Chemical Society, 1999 , vol. 121, # 14 p. 3328 - 3333

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Citation Number: 49

Abstract

A new and highly effective catalytic method for epoxide alkynylations has been developed that involves the chelation-controlled alkylation of heterosubstituted epoxides with Me3Al via pentacoordinate organoaluminum complexes by taking advantage of the exceedingly high affinity of aluminum to oxygen. For example, reaction of epoxy ether,(1-benzyloxy)-3-butene oxide (1), in toluene with PhC⋮ CLi under the influence of catalytic Me3Al (10 mol%) ...