ChemInform Abstract: The [2 + 2]-Photocycloaddition of Aromatic Aldehydes and Ketones to 3,4-Dihydro-2-pyridones: Regioselectivity, Diastereoselectivity, and Reductive Ring Opening of the Product Oxetanes.
Abstract
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ChemInform Abstract
The pyridone (II) smoothly undergoes [2 + 2]photocycloaddition with aromatic aldehydes and ketones to afford fused oxetanes with high regio- and diastereoselectivity. The oxetane ring can easily be cleaved under reduction conditions which opens up a new and efficient route to 2-arylmethyl-3-piperidinols. 4-Substituted dihydropyridones, however, are less suited alkene components in [2 + 2]photocycloaddition reactions. The facial diastereoselectivity in the conversion of the chiral aldehyde (V) is found to be controlled by hydrogen bonds.
