Strained organosilacyclic compounds: synthesis of anti-Bredt olefins and trans-dioxasilacyclooctenes

Abstract

Insertions of silylenes into the allylic carbon–oxygen bond of vinyl epoxides was shown to generate 1,2-silaoxetanes. These intermediates undergo highly diastereoselective additions to aldehydes to form anti-Bredt olefins and trans-dioxasilacyclooctenes. Additions of electrophiles could be performed selectively on the outside face of these strained trans-cycloalkenes to provide valuable functionalized compounds.