title: Asymmetric synthesis by the intramolecular haloetherification reaction of ene acetal: discrimination of prochiral dienes in cyclohexane systems.
abstract: A novel asymmetric synthesis of the cyclohexane derivative functionalized by some substituents has been developed from the diene acetals (1), prepared from the corresponding diene aldehyde and (+)-hydrobenzoin. The treatment of 1 with NBS in the presence of MeOCH2CH2OH predominantly afforded 2 in a stereoselective manner. Subsequent alkylation of the methoxyethoxy group produced the optically active cyclohexene compounds (3) in good yields. The stereoselective chemical modification of the remaining olefin in 3 was made by OsO4-oxidation.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan. fujioka@phs.osaka-u.ac.jp
authors.forename: Hiromichi
authors.initials: H
authors.lastname: Fujioka
authors.forename: Naoyuki
authors.initials: N
authors.lastname: Kotoku
authors.forename: Yoshinari
authors.initials: Y
authors.lastname: Sawama
authors.forename: Hidetoshi
authors.initials: H
authors.lastname: Kitagawa
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Ohba
authors.forename: Tsung-Lung
authors.initials: TL
authors.lastname: Wang
authors.forename: Yasushi
authors.initials: Y
authors.lastname: Nagatomi
authors.forename: Yasuyuki
authors.initials: Y
authors.lastname: Kita
mesh_terms: D000080:Acetals / Q000737:chemistry*; D003510:Cyclohexanes / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D003510:Cyclohexanes; D004987:Ethers