Abstract
3-(Silyloxy)oxetanes are obtained by irradiating mixtures of
aromatic aldehydes and silyl enol ethers in benzene as the solvent. The
reactions occur with high simple diastereoselectivity and, when
R¹ is chiral, with high facial diastereoselectivity.
Under similar conditions, but in acetonitrile rather than benzene
as the preferred solvent, the Paternò-Büchi
reaction of N -acyl enamines (enamides)
gives the corresponding protected 3-aminooxetanes. The cis -products are obtained with significant
simple diastereoselectivity.
Key words
cycloadditions - heterocycles - oxetanes - Paternò-Büchi reactions - photochemistry
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