Enhanced stereoselectivity in photoelectrocyclization of tropolone ethers via confinement in chiral inductor-modified lyotropic liquid crystals.
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.
Lv
Feng-Feng
FF
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China.
Chen
Bin
B
Wu
Li-Zhu
LZ
Zhang
Li-Ping
LP
Tung
Chen-Ho
CH
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
D019086:Bridged Bicyclo Compounds, Heterocyclic; C037100:2-methoxytropolone; D010665:Phenylpropanolamine; D014334:Tropolone