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Approach to Spirocyclohexadienes via Visible Light‐Mediated ipso‐Cyclization of Amino Acid Derivatives with N‐(2‐Phenyl)benzoyl Groups
Asian Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2024-04-16 , DOI: 10.1002/ajoc.202400140
Yuki Yoshida 1 , Haruka Takeuchi 1 , Norihito Arichi 1 , Shinya Oishi 1 , Hiroaki Ohno 2 , Shinsuke Inuki 1
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Spirocycles are important structural motifs, found in natural and pharmaceutical compounds, which have attracted considerable interest in modern drug discovery research. Herein, we describe the development of a visible light‐mediated ipso‐cyclization of amino acid derivatives with N‐(2‐phenyl)benzoyl groups, allowing easy access to a variety of spirocyclohexadienes. The addition of water was found to be beneficial in promoting the reaction progress. Investigation of the substrate scope revealed that incorporating an electron‐donating moiety at the 3'‐position of the biphenyl group resulted in a more favorable outcome for spirocycle formation.

中文翻译:

通过可见光介导的 N-(2-苯基)苯甲酰基氨基酸衍生物的原位环化制备螺环己二烯的方法

螺环是在天然和药物化合物中发现的重要结构基序,引起了现代药物发现研究的极大兴趣。在此,我们描述了具有N-(2-苯基)苯甲酰基的氨基酸衍生物的可见光介导的原环化的发展,使得可以容易地获得各种螺环己二烯。发现水的加入有利于促进反应进程。对底物范围的研究表明,在联苯基的 3' 位掺入供电子部分可以为螺环的形成带来更有利的结果。
更新日期:2024-04-16
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