Abstract
Four-carbon-tethered pyridones undergo photocycloaddition to give exclusively trans-[4 + 4] products. The presence of a tether alcohol engenders a solvent-dependent diastereoselectivity for the cycloaddition by intramolecular hydrogen bonding to the adjacent pyridone. Following cycloaddition, the alcohol can deliver a carbonyl group to the proximal, hindered amide nitrogen, leading to a very facile amide hydrolysis.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Alcohols / chemistry*
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Amides / chemistry*
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Catalysis
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Cyclization
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Hydrogen Bonding
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Hydrolysis
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Ketones / chemistry
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Models, Molecular
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Molecular Conformation
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Molecular Structure
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Photochemistry
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Pyridines / chemistry
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Pyridines / radiation effects
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Pyridones / chemistry*
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Pyridones / radiation effects
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Solvents
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Stereoisomerism
Substances
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Alcohols
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Amides
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Ketones
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Pyridines
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Pyridones
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Solvents