Área de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001 Burgos, Spain.
Beilstein J Org Chem. 2011;7:786-93. doi: 10.3762/bjoc.7.89. Epub 2011 Jun 9.
The selectivity of our previously described gold-catalyzed tandem reaction, 1,2-indole migration followed by aura-iso-Nazarov cyclization, of 3-propargylindoles bearing (hetero)aromatic substituents at both the propargylic and terminal positions, was reversed by the proper choice of the catalyst and the reaction conditions. Thus, 3-(inden-2-yl)indoles, derived from an aura-Nazarov cyclization (instead of an aura-iso-Nazarov cyclization), were obtained in moderate to good yields from a variety of 3-propargylindoles.
我们之前描述的金催化串联反应，即 3-炔丙基吲哚在偕二芳基和末端位置均带有（杂）芳基取代基时的 1,2-吲哚迁移，接着是 auraiso-Nazarov 环化，其选择性可以通过选择合适的催化剂和反应条件来反转。因此，从各种 3-炔丙基吲哚中，以中等至良好的收率获得了来自 auraiso-Nazarov 环化（而不是 aur-Nazarov 环化）的 3-（茚-2-基）吲哚。
