Ring-Opening Reactions of α,β-Epoxy Silanes with Organocopper Reagents: Reaction at Carbon or Silicon?

摘要

α,β-Epoxy silanes react with a wide variety of reagents via ring opening α to silicon. These reactions have been found to have a variety of uses in organic synthesis. A number of years ago, we introduced a stereospecific synthesis of olefins and heteroatom-substituted olefins based on these ring opening reactions coupled with stereospecific β-elimination reactions of the resulting β-hydroxy silanes. α,β-Epoxy silanes also have potential uses for the preparation of homochiral building blocks in asymmetric synthesis due to the effect of silicon on the stereochemistry of epoxidation reactions, particularly the Sharpless asymmetric epoxidation.