title: Photoreactions with a Twist: Atropisomerism-Driven Divergent Reactivity of Enones with UV and Visible Light.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, North Dakota State University, 1231 Albrecht Blvd., Fargo, ND, 58108-6050, USA.
authors.forename: Nandini
authors.initials: N
authors.lastname: Vallavoju
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, 400076, India.
authors.forename: Avadakkam
authors.initials: A
authors.lastname: Sreenithya
authors.affiliation: Department of Chemistry and Biochemistry, North Dakota State University, 1231 Albrecht Blvd., Fargo, ND, 58108-6050, USA.
authors.forename: Anoklase J-L
authors.initials: AJ
authors.lastname: Ayitou
authors.affiliation: Department of Chemistry, Columbia University, New York, NY, 10027, USA.
authors.forename: Steffen
authors.identifier: http://orcid.org/0000-0002-4592-5280
authors.initials: S
authors.lastname: Jockusch
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, 400076, India.
authors.forename: Raghavan B
authors.initials: RB
authors.lastname: Sunoj
authors.affiliation: Department of Chemistry and Biochemistry, North Dakota State University, 1231 Albrecht Blvd., Fargo, ND, 58108-6050, USA. jayaraman.sivaguru@ndsu.edu.
authors.forename: Jayaraman
authors.identifier: http://orcid.org/0000-0002-0446-6903
authors.initials: J
authors.lastname: Sivaguru
mesh_terms: D008027:Light; D015394:Molecular Structure; D010777:Photochemistry; D015363:Quinolones / Q000737:chemistry*; D013237:Stereoisomerism; D047090:beta-Lactams / Q000737:chemistry*
chemical_list: C546846:3,4-dihydroquinolin-2-one; D015363:Quinolones; D047090:beta-Lactams
keywords: asymmetric photochemistry; atropisomerism; atropselective photoreactions; enones; hydrogen abstraction; photochirogenesis