Carbene-mediated stereoselective olefination of vinyl sulfoxonium ylides with diazo compounds and acetals,Chemical Communications

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Carbene-mediated stereoselective olefination of vinyl sulfoxonium ylides with diazo compounds and acetals
Chemical Communications ( IF 4.3 ) Pub Date : 2024-03-18 , DOI: 10.1039/d4cc00450g
Dinesh Kumar Gopalakrishnan ₁ , Srashti Bhardwaj ₁ , Sandeep Kumar ₁ , Tarak Karmakar ₁ , Janakiram Vaitla ₁

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The development of stereoselective olefination using sulfur ylide-derived vinyl carbenes with diazo esters and acetals is reported. Both reactions proceed through nucleophilic addition to electrophiles at the γ-position of an in situ-generated 2-alkoxy furan intermediate. The synthetic utility of the developed method is demonstrated by the total synthesis of rubrolide E. Detailed mechanistic investigations and quantum chemical calculations provide insight into the reaction mechanism.

中文翻译：

卡宾介导的乙烯基亚鎓叶立德与重氮化合物和缩醛的立体选择性烯化反应

据报道，使用硫叶化物衍生的乙烯基卡宾与重氮酯和缩醛进行立体选择性烯化反应的发展。两个反应均通过在原位生成的 2-烷氧基呋喃中间体的 γ 位处与亲电子试剂发生亲核加成来进行。所开发方法的合成实用性通过红溴内酯 E 的全合成得到了证明。详细的机理研究和量子化学计算提供了对反应机制的深入了解。

更新日期：2024-03-18

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