Insertions of silylenes into vinyl epoxides: Diastereoselective synthesis of functionalized, optically active trans-dioxasilacyclooctenes

(Chemical Equation Presented) This communication describes a direct route to functionalized nonracemic trans-dioxasilacyclooctenes that involves stereoselective silylene insertions into vinyl epoxides to provide vinyl silaoxetane intermediates. These strained allylic silanes then undergo uncatalyzed allylation of aldehydes to afford trans-dioxasilacyclooctenes. Diastereoselective additions to these alkenes allow efficient transfer of planar chirality to chirality at stereogenic carbon atoms.