Access to Benzylic Quaternary Carbons from Aromatic Ketones,Organic Letters

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Access to Benzylic Quaternary Carbons from Aromatic Ketones
Organic Letters ( IF 4.9 ) Pub Date : 2019-07-16 00:00:00 , DOI: 10.1021/acs.orglett.9b02204
You Li ₁ , Jingpeng Han ₂ , Han Luo ₂ , Qiaoyu An ₂ , Xiao-Ping Cao ₁ , Baosheng Li _{1,

2}

Affiliation

The construction of benzylic all-carbon quaternary stereocenters, which are ubiquitous in biomolecules and drugs, is a task of high practical significance. Herein, we disclose a highly efficient one-pot method of constructing all-carbon quaternary structural units from aryl ketones, revealing that the entire process involves three consecutive chemical events, namely nucleophilic addition, Meinwald 1,2-hydrogen migration, and alkylation. Interestingly, dimerization of acetophenones results in formation of 2,4-diarylfurans under the employed conditions rather than the quaternary carbon products.

中文翻译：

从芳族酮中获取苄基季碳

在生物分子和药物中普遍存在的苄基全碳四元立体中心的构建是具有高度实际意义的任务。在这里，我们公开了一种由芳基酮构建全碳四元结构单元的高效一锅法，揭示了整个过程涉及三个连续的化学事件，即亲核加成，Meinwald 1,2-氢迁移和烷基化。有趣的是，在所采用的条件下，苯乙酮的二聚作用导致形成2，4-二芳基呋喃，而不是季碳产物。

更新日期：2019-07-16

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