Diastereoselective Synthesis of Dibenzo[b,d]azepines by Pd(II)-Catalyzed [5+2] Annulation of o-Arylanilines with Dienes

Diastereoselective Synthesis of Dibenzo[b,d]azepines by Pd(II)-Catalyzed [5+2] Annulation of o-Arylanilines with Dienes
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Pd(II) 催化非对映选择性合成二苯并[b,d]氮杂环庚烷 [5 2] 邻芳基苯胺与二烯的环化

DOI:
10.1021/acs.orglett.7b00503
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发表时间:
2017-04-07
期刊:
影响因子:
5.2
通讯作者:
Luan, Xinjun
Luan, Xinjun
中科院分区:
化学1区
文献类型:
--
作者:
Bai, Lu;Wang, Yan;Luan, Xinjun

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描述了一种以高度非对映选择性的方式构建含有两个不同立体元素的二苯并[B,d]氮杂卓的有效方法。[5 + 2]反应的关键是通过连续的C-H活化和二烯的区域特异性迁移插入形成π-烯丙基alladitin物种。这一观察结果与通常通过β-氢化物消除直接进行烯基化的1,2-烯烃的行为形成对比。
An efficient method for the construction of dibenzo [b,d]azepines containing two distinct stereogenic elements in a highly diastereoselective fashion is described. The key of the [5 + 2] reaction is to form a pi-allylialladitin species through sequential C-H activation and regiospecific migratory insertion of the diene.This observation contrasts with the behavior of 1,2-alkenes that generally underwent direct alkenylation via beta-hydride elimination.