title: Stereoselective synthesis of tetrasubstituted olefins through a halogen-induced 1,2-silyl migration.
abstract: Migrating through Si valley: The highly stereoselective formation of α-silyl-β- haloenones by way of silicon group migration is described. Electrophilic activation of the alkyne by N-halosuccinimides induced an anti-selective migration to give highly substituted enones (see scheme). These enone products can be readily converted to the all-carbon tetrasubstituted alkenes while maintaining their geometry.
authors.affiliation: Department of Chemistry, Colorado State University, 1872 Campus Delivery, Fort Collins, CO 80523, USA.
authors.forename: Nicholas T
authors.initials: NT
authors.lastname: Barczak
authors.forename: Douglas A
authors.initials: DA
authors.lastname: Rooke
authors.forename: Zachary A
authors.initials: ZA
authors.lastname: Menard
authors.forename: Eric M
authors.initials: EM
authors.lastname: Ferreira
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D006219:Halogens / Q000737:chemistry*; D012825:Silicon / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000480:Alkynes; D006219:Halogens; D012825:Silicon
keywords: alkene geometry; alkynes; halosilylation; migration; stereoselectivity