A Zn(OTf)2 catalyzed Ugi-type reaction of 3-(2-isocyanoethyl)indoles with indole-derived ketimines: rapid access to hexacyclic spiroindolines†,Organic Chemistry Frontiers

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A Zn(OTf)2 catalyzed Ugi-type reaction of 3-(2-isocyanoethyl)indoles with indole-derived ketimines: rapid access to hexacyclic spiroindolines†
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2018-06-08 00:00:00 , DOI: 10.1039/c8qo00382c
Yun-Lin Liu _{1,

2,

3,

4} , Xiang-Yu Mao _{1,

2,

3,

4} , Xiao-Tong Lin _{1,

2,

3,

4} , Guo-Shu Chen _{1,

2,

3,

4}

Affiliation

We report a Zn(OTf)₂ catalyzed Ugi-type reaction of 3-(2-isocyanoethyl)indoles and indole-derived ketimines to rapidly afford hexacyclic spiroindolines featuring three stereocenters including two quaternary stereocenters in moderate to excellent yields (30–89%) with complete diastereoselectivity. This reaction is highly efficient because two C–C and one C–N bonds as well as two new rings are created under mild reaction conditions in a single step.

中文翻译：

Zn（OTf）₂催化3-（2-异氰乙基）吲哚与吲哚衍生的酮亚胺的Ugi型反应：快速获得六环螺二吲哚†

我们报道了Zn（OTf）₂催化的3-（2-异氰乙基）吲哚和吲哚衍生的酮亚胺的Ugi型反应，以迅速提供具有三个立体中心的六环螺二氢吲哚，包括两个中等至极好的立体中心（四元立体中心）（30-89％）具有完全的非对映选择性。该反应非常有效，因为在温和的反应条件下，只需一步即可生成两个C–C和一个C–N键以及两个新的环。

更新日期：2018-06-08

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