Photoreactions with a Twist: Atropisomerism-Driven Divergent Reactivity of Enones with UV and Visible Light.
Nandini VallavojuAvadakkam SreenithyaAnoklase J-L AyitouSteffen JockuschRaghavan B SunojJayaraman SivaguruPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2016)
Light-induced transformation of atropisomeric and achiral enones displays divergent reactivity. Photocyclization leading to 3,4-dihydroquinolin-2-one was observed with achiral enone carboxamide, whereas the atropisomeric enone carboxamides underwent hydrogen abstraction leading to spiro-β-lactams. Detailed photochemical, photophysical, and theoretical investigations have provided insight into this divergent reactivity and selectivity.