title: Stereoselective synthesis of bicyclo[3.1.1]heptane derivatives via intramolecular photocycloaddition reaction.
abstract: Optically active 1,3-bridged cyclobutanes 10 of the bicyclo[3.1.1]heptane ring system and 1,2-bridged cyclobutanes 11 of the bicyclo[3.2.0]heptane ring system were produced by UV irradiation of alpha,beta,gamma,delta-unsaturated esters 9a and 9c-f. The preference of endo-stereochemistry at C-6 bridged head was observed in cross-adducts 10. On the other hand, irradiation of conjugated dienol 9b led via only parallel cycloaddition to 1,2-bridged cyclobutane 11.
authors.affiliation: Graduate School of Environment and Information Sciences, Yokohama National University, Tokiwadai 79-5, Hodogaya-ku, Yokohama 240-8501, Japan. k-honda@ynu.ac.jp
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Honda
authors.forename: Mari
authors.initials: M
authors.lastname: Konishi
authors.forename: Manabu
authors.initials: M
authors.lastname: Kawai
authors.forename: Akihisa
authors.initials: A
authors.lastname: Yamada
authors.forename: Yasuhiko
authors.initials: Y
authors.lastname: Takahashi
authors.forename: Yujiro
authors.initials: Y
authors.lastname: Hoshino
authors.forename: Seiichi
authors.initials: S
authors.lastname: Inoue
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D006536:Heptanes / Q000138:chemical synthesis*; D055668:Photochemical Processes; D013237:Stereoisomerism
chemical_list: D001643:Bridged Bicyclo Compounds; D006536:Heptanes