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 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.
Prévost
Michel
M
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
Woerpel
K A
KA
D004852:Epoxy Compounds / Q000737:chemistry*; D009795:Octanes / Q000138:chemical synthesis*; D012821:Silanes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D004852:Epoxy Compounds; D009795:Octanes; D012821:Silanes; D014753:Vinyl Compounds