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[2 + 2] Photochemical Cycloaddition/Ring Opening of 6-Alkenyl-2,3-dihydro-4-pyridones

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posted on 01.10.2010 by James J. Sahn, Daniel L. Comins
During the course of a study aimed at constructing azaspirocycles from 2,3-dihydro-4-pyridones, an unexpected product was obtained in the SET ring-opening reaction of photocycloadduct 1. Differences in reactivity between homologues 1 and 2 were observed in the presence of SmI2. Tricyclic ketone 2 afforded azaspiro[5.5]undecane 15 when treated with SmI2; however, when ketone 1 was submitted to similar reaction conditions a double ring-opening/reduction sequence gave cis-piperidinol 10.