不对称形式的烯基取代杂芳基和芳基醛的烯基亚胺离子活化。
Asymmetric Formal Vinylogous Iminium Ion Activation for Vinyl-Substituted Heteroaryl and Aryl Aldehydes.
机构信息
Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy , Sichuan University , Chengdu 610041 , China.
Institute of Organic Chemistry, Department of Chemistry , Lodz University of Technology , Zeromskiego 116 , 90-924 Lodz , Poland.
出版信息
Org Lett. 2019 Dec 6;21(23):9628-9632. doi: 10.1021/acs.orglett.9b03794. Epub 2019 Nov 25.
The vinyl group tethered to furfurals could be LUMO-lowered by forming formal vinylogous iminium ion intermediates catalyzed by a chiral secondary amine and underwent asymmetric [3 + 2] cycloaddition reactions with -trifluoroethyl-substituted isatin imines, furnishing a variety of spirooxindoles incorporating a 3,2'-pyrrolidine motif with excellent stereoselectivity. In addition, this strategy has been successfully expanded to a number of vinyl-substituted electron-rich heteroaryl aldehydes and even some specific aryl aldehydes.
与呋喃甲醛相连的乙烯基可以通过形成由手性仲胺催化的形式乙烯基亚胺离子中间体来降低 LUMO，并且与 -三氟乙基取代的靛红亚胺进行不对称 [3+2] 环加成反应，生成各种具有 3,2'-吡咯烷骨架的螺环氧化吲哚，具有优异的立体选择性。此外，该策略已成功扩展到许多乙烯基取代的富电子杂芳基醛，甚至一些特定的芳基醛。
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