title: Catalytic diastereoselective polycyclization of homo(polyprenyl)arene analogues bearing terminal siloxyvinyl groups.
abstract: Highly diastereoselective polycyclization of homo(polyprenyl)arene analogues bearing terminal siloxyvinyl groups was catalyzed by tin(IV) chloride (10 mol %). The cyclizations of tert-butyldiphenylsilyl and triisopropylsilyl polyenol ethers gave 4alpha(equatorial)- and 4beta(axial)-siloxypolycycles as major isomers, respectively. The strong nucleophilicity of pro-C(9), a (6E) geometry, and a bulky silyl group effectively favored the alpha-preference, whereas the weak nucleophilicity of pro-C(9), a (6Z)-geometry, and less steric hindrance of a silyl group favored the beta-preference. [reaction: see text].
authors.affiliation: Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan.
authors.forename: Muhammet
authors.initials: M
authors.lastname: Uyanik
authors.forename: Kazuaki
authors.initials: K
authors.lastname: Ishihara
authors.forename: Hisashi
authors.initials: H
authors.lastname: Yamamoto
mesh_terms: D002384:Catalysis; D003500:Cyclization; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis*; D017971:Tin Compounds / Q000737:chemistry
chemical_list: D013729:Terpenes; D017971:Tin Compounds; C023599:stannous chloride