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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
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Bridged Bicyclo Compounds, Heterocyclic / chemistry
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Bridged Bicyclo Compounds, Heterocyclic / radiation effects
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Cyclization
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Electrochemistry
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Liquid Crystals / chemistry*
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Molecular Structure
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Phenylpropanolamine / chemistry*
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Photochemistry
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Stereoisomerism
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Tropolone / analogs & derivatives*
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Tropolone / chemistry
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Tropolone / radiation effects
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Ultraviolet Rays
Substances
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Bridged Bicyclo Compounds, Heterocyclic
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2-methoxytropolone
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Phenylpropanolamine
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Tropolone