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

Photoreactions with a Twist: Atropisomerism-Driven Divergent Reactivity of Enones with UV and Visible Light.
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DOI:
10.1002/chem.201601509
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发表时间:
2016-08
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通讯作者:
N. Vallavoju;A. Sreenithya;A. Ayitou;S. Jockusch;R. B. Sunoj;J. Sivaguru
N. Vallavoju;A. Sreenithya;A. Ayitou;S. Jockusch;R. B. Sunoj;J. Sivaguru
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作者:
N. Vallavoju;A. Sreenithya;A. Ayitou;S. Jockusch;R. B. Sunoj;J. Sivaguru

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光诱导的阻转异构体和非手性烯酮转化表现出不同的反应性。使用非手性烯酮甲酰胺观察到光环化产生 3,4-二氢喹啉-2-酮,而阻转异构体烯酮甲酰胺则经历氢提取,产生螺-β-内酰胺。详细的光化学、光物理和理论研究提供了对这种不同反应性和选择性的见解。
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.