Li DingXi, Park Yeji, Yun Jaesook
Department of Chemistry and Institute of Basic Science , Sungkyunkwan University , Suwon 440-746 , Korea.
Org Lett. 2018 Dec 7;20(23):7526-7529. doi: 10.1021/acs.orglett.8b03286. Epub 2018 Nov 14.
A practical regioselective and diastereoselective synthesis of functionalized 1-benzo[ b]azepines by copper-catalyzed intramolecular cyclization has been developed. The reaction involves borylcupration of a mixture of ( E/ Z)-1,3-dienes, followed by capture of the generated ( Z)-allylcopper species with an imine to produce 7-membered N-heterocycles as single diastereomers. The reaction is applicable to various ( E/ Z)-dienyl arenes with an imine moiety at the ortho-position, including aryl, alkyl, and heterocyclic aldimines, and ketimines, affording borylated 2,3- cis-substituted 1-benzo[ b]azepines in good yields.
通过铜催化的分子内环化反应，已开发出一种实用的区域选择性和非对映选择性合成功能化1-苯并[b]氮杂䓬的方法。该反应包括对（E/Z）-1,3-二烯混合物进行硼铜化反应，然后用亚胺捕获生成的（Z）-烯丙基铜物种，以生成单一非对映异构体的七元氮杂环。该反应适用于各种在邻位带有亚胺部分的（E/Z）-二烯基芳烃，包括芳基、烷基和杂环醛亚胺以及酮亚胺，能以良好的产率得到硼化的2,3-顺式取代的1-苯并[b]氮杂䓬。
