The tricyclo [2.1.0.0~(2,5)] pentan-3-one system: a new probe for the study of pi-facial selectivity in nucleophilic additions

摘要

Monosubstituted tricyclo [2.1.0.0~(2,5)] pentan-3-one derivatives have been synthesised and subjected to hydride reduction. Quite unexpectedly and in contrast to earlier observations in related systems, anti-selectivity has been encountered in these substrates. Computational studies employing various models reproduce the observed facial preference and indicate that the causative factor for the anti-preference could be the polarization of the C1-C5 strained sigma bond.