4.9 C–C Bond Formation using Lewis Acids and Silicon Enolates

Abstract

The asymmetric carbon–carbon bond-forming reaction is one of the most powerful and useful methods to synthesize optically active and highly functionalized complex molecules such as biologically active compounds. In particular, asymmetric reactions of enol derivatives, including vinyl ethers, have been well investigated and have established an essential position in asymmetric synthetic methodology. Among them, silicon enolates have been well investigated as an isolable but reactive enol component in stereoselective synthesis, especially in asymmetric catalysis using chiral Lewis acids. Several kinds of chiral metal Lewis acids were developed and successfully applied for highly stereoselective synthesis of optically active molecules. In this chapter, the development of asymmetric carbon–carbon bond-forming reactions using silicon enolates and chiral metal Lewis acids is summarized.