Synthetic applications of cycloaddition of silylene

Abstract

In this short review, a new methodology of preparation of the silacyclic compounds using silylene and their application for organic synthesis are described. Silylene transfer from silacyclopropane to alkene, alkyne, imine, and α, β-unsaturated carbonyl compounds was catalyzed by silver salt to give the corresponding [1+2] or [1+4] cycloadducts in good yields. Combination of the cycloaddition, Ireland-Claisen rearrangement, and oxidative cleavage of silicon-carbon bond provided the regio-and stereoselective synthesis of polyol and alpha;-hydroxyacid in a mild condition.