State Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering , Lanzhou University , 222 South Tianshui Road , Lanzhou , 730000 , P. R. China.
School of Chemistry and Chemical Engineering , Chongqing University , 174 Shazheng Street , Chongqing , 400030 , P. R. China.
Org Lett. 2019 Aug 2;21(15):6050-6053. doi: 10.1021/acs.orglett.9b02204. Epub 2019 Jul 16.
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.
构建苄基全碳季碳中心是一项具有重要实际意义的任务，苄基全碳季碳中心普遍存在于生物分子和药物中。在此，我们公开了一种从芳基酮高效构建全碳季碳结构单元的一锅法，整个过程涉及三个连续的化学反应事件，即亲核加成、Meinwald 1,2-氢迁移和烷基化。有趣的是，在所用条件下，苯乙酮的二聚化导致 2,4-二芳基呋喃的形成，而不是季碳产物。
