title: Synthesis of 3,4-dimethylidene oxacycles through Prins-type cyclization of allenylmethylsilanes.
abstract: An efficient synthesis of 3,4-dimethylidene oxacycles including oxolanes and oxepanes through Prins-type cyclization of hydroxy(allenylmethyl)silanes is described. We have shown that 2-substituted tetrahydrofuran derivatives could be produced by using this strategy although the 5-endo-trig cyclization mode is stereoelectronically disfavored. We also applied our method to the stereoselective synthesis of 2,7-cis-3,4-dimethylidene oxepanes, which were used for constructing more complex ring systems, such as polyether bicycles or tricycles.
authors.affiliation: Center for Neuro-Medicine, Korea Institute of Science and Technology (KIST), Hwarangno 14-gil, Seongbuk-gu, Seoul, 136-791, South Korea.
authors.forename: Punna Reddy
authors.initials: PR
authors.lastname: Ullapu
authors.forename: Young Seub
authors.initials: YS
authors.lastname: Kim
authors.forename: Jae Kyun
authors.initials: JK
authors.lastname: Lee
authors.forename: Ae Nim
authors.initials: AN
authors.lastname: Pae
authors.forename: Youseung
authors.initials: Y
authors.lastname: Kim
authors.forename: Sun-Joon
authors.initials: SJ
authors.lastname: Min
authors.forename: Yong Seo
authors.initials: YS
authors.lastname: Cho
mesh_terms: D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006571:Heterocyclic Compounds; D012821:Silanes