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Catalytic bimetalic [Pd(0)/Ag(I) Heck-1,3-dipolar cycloaddition cascade reactions accessing spiro-oxindoles. Concomitant in situ generation of azomethine ylides and dipolarophile
Tetrahedron ( IF 2.1 ) Pub Date : 2018-05-24 , DOI: 10.1016/j.tet.2018.05.017
Emma L. Millington , H. Ali Dondas , Colin W.G. Fishwick , Colin Kilner , Ron Grigg

Spiro-oxindoles, epi-Spirotryprostatin A and its analogues were prepared from a tactical combination of cascade catalytic bimetallic Pd (0)/Ag(I), intramolecular Heck and subsequent imine → azomethine ylide 1,3-Dipolar cycloaddition reactions. The cascade features in situ generation of azomethine ylides and dipolarophiles and produces two new rings together with three stereocentres in good to excellent yields.



中文翻译:

催化双金属[Pd(0)/ Ag(I)Heck-1,3-偶极环加成级联反应访问螺-羟吲哚。伴随原位代甲亚胺叶立德和亲偶极的

从级联催化双金属Pd(0)/ Ag(I),分子内Heck以及随后的亚胺→亚甲次基叶立德 1,3-偶极环加成反应的战术组合制备螺-羟吲哚,epi-Spirotryprostatin A及其类似物。级联反应具有原位生成甲亚胺基亚胺和双极性亲核试剂的特性,并产生两个新的环以及三个立体中心,收率好至极好。

更新日期:2018-05-24
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