化学
分子间力
环加成
反应性(心理学)
氮杂环丁烷
组合化学
光化学
计算化学
分子
有机化学
催化作用
医学
病理
替代医学
作者
M. Becker,Emily R. Wearing,Corinna S. Schindler
出处
期刊:Nature Chemistry
[Springer Nature]
日期:2020-09-23
卷期号:12 (10): 898-905
被引量:126
标识
DOI:10.1038/s41557-020-0541-1
摘要
Intermolecular [2+2] photocycloadditions represent a powerful method for the synthesis of highly strained, four-membered rings. Although this approach is commonly employed for the synthesis of oxetanes and cyclobutanes, the synthesis of azetidines via intermolecular aza Paternò–Büchi reactions remains highly underdeveloped. Here we report a visible-light-mediated intermolecular aza Paternò–Büchi reaction that utilizes the unique triplet state reactivity of oximes, specifically 2-isoxazoline-3-carboxylates. The reactivity of this class of oximes can be harnessed via the triplet energy transfer from a commercially available iridium photocatalyst and allows for [2+2] cycloaddition with a wide range of alkenes. This approach is characterized by its operational simplicity, mild conditions and broad scope, and allows for the synthesis of highly functionalized azetidines from readily available precursors. Importantly, the accessible azetidine products can be readily converted into free, unprotected azetidines, which represents a new approach to access these highly desirable synthetic targets. Although azetidines represent highly desirable building blocks in drug discovery, methods for their efficient and straightforward synthesis remain underdeveloped. Now, it has been shown that highly functionalized azetidines can be prepared via an intermolecular [2+2] photocycloaddition reaction between cyclic oximes and alkenes, in a process enabled by a visible-light-mediated triplet energy transfer.
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