Insertions of Silylenes into Vinyl Epoxides: Diastereoselective Synthesis of Functionalized, Optically Active trans-Dioxasilacyclooctenes

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