title: Regioselective prins cyclization of allenylsilanes. Stereoselective formation of multisubstituted heterocyclic compounds.
abstract: The Prins cyclization of hydroxy or amino group-containing allenylsilanes with carbonyl compounds occurred at the allenic terminus in a regio- and stereoselective manner to give the di- or trisubstituted tetrahydrofurans, tetrahydropyrans, and pyrrolidines. During the reaction, the allenic axial chirality of the starting material was efficiently transferred to the newly formed carbon chiral centers of the product.
authors.affiliation: Graduate School of Science, Osaka City University, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan.
authors.forename: Takuya
authors.initials: T
authors.lastname: Okada
authors.forename: Airi
authors.initials: A
authors.lastname: Shimoda
authors.forename: Tetsuro
authors.initials: T
authors.lastname: Shinada
authors.forename: Kazuhiko
authors.initials: K
authors.lastname: Sakaguchi
authors.forename: Yasufumi
authors.initials: Y
authors.lastname: Ohfune
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; D000480:Alkynes; D005663:Furans; D012821:Silanes