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.
College of Pharmacy, Third Military Medical University, Shapingba, Chongqing 400038, China.
Chem Commun (Camb). 2021 Sep 9;57(72):9056-9059. doi: 10.1039/d1cc03830c.
The previously unreported zwitterionic -allylic ylide species from the corresponding Morita-Baylis-Hillman carbonates of trifluoromethyl ketones and acrylonitrile are generated under the catalysis of cinchona-derived tertiary amines, and subsequently participate in switchable asymmetric [3+2] or [4+1] annulations with 1-azadienes in chemo-, regio-, and stereodivergent manners catalyst or substrate control. A diverse range of frameworks, having a trifluoromethylated all-carbon quaternary stereogenic centre or a tetrasubstituted alkene moiety, are generally constructed in good yields with excellent enantioselectivity.
先前未报道的三氟甲基酮和丙烯腈相应的 Morita-Baylis-Hillman 碳酸酯的两性烯丙基叶立德物种在金鸡纳衍生的叔胺催化下生成，随后以化学、区域和立体发散的方式与 1-氮杂二烯进行可切换的不对称[3+2]或[4+1]环加成。通过催化剂或底物控制，通常可以以良好的收率和优异的对映选择性构建具有三氟甲基化全碳季碳手性中心或四取代烯烃部分的各种骨架。
