Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry , Sichuan University , Chengdu 610064 , China.
Org Lett. 2020 Feb 21;22(4):1390-1395. doi: 10.1021/acs.orglett.0c00004. Epub 2020 Jan 28.
A highly efficient asymmetric imino-ene reaction of cyclic ketimines with silyl enol ethers was developed. Various chiral benzosultam derivatives were obtained in excellent yields (up to 99%), enantioselectivities (up to 99% ee), and diastereoselectivities (up to >19:1 dr) by utilizing a Ni(BF)·6HO/,-dioxide complex as the catalyst. A possible transition state model was proposed to explain the stereoinduction. Furthermore, the synthetic utility of the protocol provided quick access to optically pure HIV-1 inhibitor.
发展了一种高效的环状亚胺与硅基烯醇醚的不对称亚胺-ene 反应。利用 Ni(BF)·6H2O/手性双噁唑啉配体作为催化剂，各种手性苯并恶唑烷酮衍生物以优异的收率（高达 99%）、对映选择性（高达 99%ee）和非对映选择性（高达 >19:1 dr）得到。提出了一个可能的过渡态模型来解释立体诱导。此外，该方法的合成实用性为快速获得光学纯 HIV-1 抑制剂提供了途径。
