Photoreactions with a Twist: Atropisomerism‐Driven Divergent Reactivity of Enones with UV and Visible Light

Vallavoju, Nandini; Sreenithya, Avadakkam; Ayitou, Anoklase J. ‐L.; Jockusch, Steffen; Sunoj, Raghavan B.; Sivaguru, Jayaraman

doi:10.1002/chem.201601509

Title: Photoreactions with a Twist: Atropisomerism‐Driven Divergent Reactivity of Enones with UV and Visible Light

Journal Article · 06 July 2016 · Chemistry - A European Journal

DOI: https://doi.org/10.1002/chem.201601509 · OSTI ID:1400573

Vallavoju, Nandini ^[1]; Sreenithya, Avadakkam ^[2]; Ayitou, Anoklase J. ‐L. ^[1];

^[3]; Sunoj, Raghavan B. ^[2];

^[1]

Department of Chemistry and Biochemistry North Dakota State University 1231 Albrecht Blvd. Fargo ND 58108-6050 USA
Department of Chemistry Indian Institute of Technology Bombay Mumbai 400076 India
Department of Chemistry Columbia University New York NY 10027 USA

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.

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Sponsoring Organization:: USDOE

Grant/Contract Number:: SC0001717

OSTI ID:: 1400573

Journal Information:: Chemistry - A European Journal, Journal Name: Chemistry - A European Journal Journal Issue: 32 Vol. 22; ISSN 0947-6539

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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