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Photoreactions with a Twist: Atropisomerism‐Driven Divergent Reactivity of Enones with UV and Visible Light
Author(s) -
Vallavoju Nandini,
Sreenithya Avadakkam,
Ayitou Anoklase J.L.,
Jockusch Steffen,
Sunoj Raghavan B.,
Sivaguru Jayaraman
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201601509
Subject(s) - reactivity (psychology) , atropisomer , chemistry , enone , photochemistry , hydrogen atom abstraction , selectivity , stereochemistry , hydrogen , organic chemistry , catalysis , medicine , alternative medicine , pathology
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.