title: Enhanced stereoselectivity in photoelectrocyclization of tropolone ethers via confinement in chiral inductor-modified lyotropic liquid crystals.
abstract: Photochemistry of tropolone methyl ether ( 1) and optically pure ( S)-tropolone-2-methylbutyl ether ( 4) has been examined in lyotropic liquid crystals (LCs) in the presence of a chiral inductor. LCs significantly enhance the influence of chiral inductors during the photoelectrocyclization of the tropolone ethers. Chiral inductors that lead to 1:1 mixtures of enantiomers or diastereomers in solution give products in up to 40% enantiomeric excess for 1 and 35% diastereomeric excess for 4 in LCs.
authors.affiliation: Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China.
authors.forename: Feng-Feng
authors.initials: FF
authors.lastname: Lv
authors.forename: Bin
authors.initials: B
authors.lastname: Chen
authors.forename: Li-Zhu
authors.initials: LZ
authors.lastname: Wu
authors.forename: Li-Ping
authors.initials: LP
authors.lastname: Zhang
authors.forename: Chen-Ho
authors.initials: CH
authors.lastname: Tung
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D003500:Cyclization; D004563:Electrochemistry; D050866:Liquid Crystals / Q000737:chemistry*; D015394:Molecular Structure; D010665:Phenylpropanolamine / Q000737:chemistry*; D010777:Photochemistry; D013237:Stereoisomerism; D014334:Tropolone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000528:radiation effects; D014466:Ultraviolet Rays
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; C037100:2-methoxytropolone; D010665:Phenylpropanolamine; D014334:Tropolone