文献类型：期刊文献

英文题名：Facile Installation of 2-Reverse Prenyl Functionality into Indoles by a Tandem N-Alkylation-Aza-Cope Rearrangement Reaction and Its Application in Synthesis

作者：Chen, Xiaobei[1,2];Fan, Huaqiang[1];Zhang, Shilei[2,3];Yu, Chenguang[2];Wang, Wei[1,2]

机构：[1]E China Univ Sci & Technol, Sch Pharm, 130 Mei Long Rd, Shanghai 200237, Peoples R China;[2]Univ New Mexico, Dept Chem & Chem Biol, MSC03 2060, Albuquerque, NM 87131 USA;[3]Soochow Univ, Coll Pharmaceut Sci, 199 Renai Rd, Suzhou 215123, Peoples R China

年份：2016

卷号：22

期号：2

起止页码：716

外文期刊名：CHEMISTRY-A EUROPEAN JOURNAL

收录：;EI(收录号：20154801606293);WOS:【SCI-EXPANDED(收录号:WOS:000368903200033)，CCR-EXPANDED(收录号:WOS:000368903200033)】；

基金：Financial support for this research from the National Science Foundation of China (no. 21372073), the Fundamental Research Funds of East China University of Science & Technology, East China University of Science & Technology, and the NSF (CHE-1057569) is gratefully acknowledged.

语种：英文

外文关键词：alkaloids; domino reactions; natural products; rearrangement; synthesis design

摘要：An unprecedented tandem N-alkylation-ionic aza-Cope (or Claisen) rearrangement-hydrolysis reaction of readily available indolyl bromides with enamines is described. Due to the complicated nature of the two processes, an operationally simple N-alkylation and subsequent microwave-irradiated ionic aza-Cope rearrangement-hydrolysis process has been uncovered. The tandem reaction serves as a powerful approach to the preparation of synthetically and biologically important, but challenging, 2-reverse quaternary-centered prenylated indoles with high efficiency. Notably, unusual nonaromatic 3-methylene-2,3-dihydro-1H-indole archi-tectures, instead of aromatic indoles, are produced. Furthermore, the aza-Cope rearrangement reaction proceeds highly regioselectively to give the quaternary-centered reverse prenyl functionality, which often produces a mixture of two regioisomers by reported methods. The synthetic value of the resulting nonaromatic 3-methylene-2,3-dihydro-1H-indole architectures has been demonstrated as versatile building blocks in the efficient synthesis of structurally diverse 2-reverse prenylated indoles, such as indolines, indolefused sultams and lactams, and the natural product bruceolline D.