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 forthe cycloaddition by intramolecular hydrogen bonding to the adjacent pyridone. Followingcycloaddition, the alcohol can deliver a carbonyl group to the proximal, hindered amide nitrogen,leading to a very facile amide hydrolysis.
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