From Protected -Hydroxy Acylsilanes to Functionalized Silyl Enol Ethers and Applications in Mukaiyama Aldol Reactions
Abstract
By starting from protected -hydroxy acylsilanes, two complementary strategies were designed to prepare stereoselectively either E or Z silyl enol ethers. These routes exhibit good tolerance for different substituents on the starting aldol-type product, as well as the choice of the hydroxyl-protecting group and the acylsilane moiety. Further, by varying the nature of the sulfone used in these reactions it proved possible to introduce different substituents on the enol ether system. Representative examples of Mukaiyama aldol reactions were performed to demonstrate the usefulness of this approach towards polypropionate fragments