Influence of the trimethylsilyl group on the diastereoselectivity of an adjacent Claisen amide-acetal rearrangement
Abstract
In contrast to their reactions with other (E)-allylic alcohols, the amide-acetals (1a, b) react with (E)-1-trimethylsilylpent-3-en-2-ol to give mixtures of product amides in which the threo-diasteroisomers marginally predominate.