Visible Light and Molecular Iodine‐Mediated Diastereoselective Intermolecular Lactonization of Styrenes with Carbonyls,Asian Journal of Organic Chemistry

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Visible Light and Molecular Iodine‐Mediated Diastereoselective Intermolecular Lactonization of Styrenes with Carbonyls
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2020-03-04 , DOI: 10.1002/ajoc.202000041
Karin Oe ₁ , Mayuki Goto ₁ , Saki Maejima ₁ , Eiji Yamaguchi ₁ , Akichika Itoh ₁

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γ‐Lactones and their derivatives show diverse biological activities, and lactone skeletons are found in various naturally occurring products, pharmaceuticals, and agrochemicals. Although there are hundreds of methodologies for synthesizing γ‐lactone, the methods that are straightforward, environmentally friendly, and stereoselective are almost unknown. In this study, the molecular iodine/visible light‐mediated highly cis‐diastereoselective lactonization reaction of styrenes with Meldrum's acid was achieved. The developed reaction proceeded with the formation of a C−C bond at the olefin's β‐position and a C−O bond at its α‐position via a single‐step reaction with high diastereoselectivity and moderate‐to‐good yield.

中文翻译：

苯乙烯与羰基的可见光和分子碘介导的非对映选择性分子间烯化

γ-内酯及其衍生物具有多种生物活性，内酯骨架存在于各种天然产物，药物和农用化学品中。尽管有数百种合成γ-内酯的方法，但几乎不知道直接，环保和立体选择性的方法。在这项研究中，实现了苯乙烯与Meldrum酸的分子碘/可见光介导的高度顺式-非对映选择性内酯化反应。发达的反应通过高非对映选择性和中等至良好收率的一步反应，在烯烃的β位形成一个C-C键，在其α位形成一个C-O键。

更新日期：2020-04-21

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