Abstract
Irradiation of 2-substituted 4-oxo-4-phenyl-butanoic amide 1a and esters 1b– f affords the corresponding cyclobutanols 4, 5 and 6. The diastereoselectivity of photocyclization depends on carboxyl and γ-substituents. In the case of pyrrolidide 10 products 13 and 14 which are formed via a competitive ε-hydrogen transfer are obtained along with 2, 11 and 12 which are the result of γ-hydrogen abstraction. The relative configurations of the photoproducts 4– 6 and 12– 14 are established by NMR and X-ray analysis.
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