Bicyclic Piperidines via [2 + 2] Photocycloaddition

J. Org. Chem. 2021, 86 (3), 2200-2209

DOI: 10.1021/acs.joc.0c02355

Shcherbakova V.; Dibchak D.; Snisarenko M.; Skalenko Y.; Denisenko A.; Kuznetsova A.; Mykhailiuk P.

A synthetic strategy to fused bicyclic piperidines—building blocks for medicinal chemistry—is developed. The key step was an intramolecular [2 + 2]-photocyclization. The photochemical step was performed on a gram scale. Crystallographic analysis of the obtained compounds revealed that they occupy a novel chemical space and can be considered as elongated analogues of 3-substituted piperidines.

Bicyclic Piperidines via [2 + 2] Photocycloaddition