Abstract

An efficient, atom economical, one-pot synthesis of endo’- selective (dispiro 3,2′-pyrrolidinyl) bisoxindole containing three contiguous chiral stereocenters with two contiguous quaternary spirostereo centers have been achieved by three-component reaction of isatins, malononitrile (cyanoacetic ester) and 1,3-dicarbonyl compounds in water in the presence of L-proline. One-pot, azomethine ylide cycloaddition with a dipolarophile without using any catalyst have also been achieved in good yields. This new methodology offers many advantages of catalyst-free, mild reaction conditions, shorter reaction time, environmental friendliness, regio- and stereoselective processes in higher yields.

Graphic abstract

Synopsis: One-pot, azomethine ylide cycloaddition with a dipolarophile without using any catalyst provides endo’- selective (dispiro 3,2′-pyrrolidinyl) bisoxindole containing three contiguous chiral stereocenters with two contiguous quaternary spirostereo centers have been achieved in good yield. The reactions preceded under mild reaction conditions without any catalyst yields high regio- and stereoselective products up to 55–99%.

中文翻译：

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高效的endo'-选择性合成（dispiro 3,2'-吡咯烷基）双恶吲哚，其中包含三个连续的手性立体中心和两个连续的季螺甾中心

摘要

高效的，原子经济的一锅合成内含选择性的（dispiro 3,2'-pyrrolidinyl）bisoxindole包含三个连续的手性立体中心和两个连续的季螺立体中心的方法是通过靛红，丙二腈（氰基乙腈）的三组分反应实现的脯氨酸的存在下，在水中的1,3-二羰基化合物）。在不使用任何催化剂的情况下，用双极性亲和剂进行一锅的甲亚胺叶立德环加成反应也已经获得了良好的收率。这种新方法具有许多优点，即无催化剂，反应条件温和，反应时间短，环境友好，区域选择性和立体选择性过程的产率更高。

图形摘要

简介：在不使用任何催化剂的情况下，使用偶极亲和剂与一锅偶氮亚胺叶立德环加成反应，可实现内含选择性（双螺3,2'-吡咯烷基）双异吲哚，其中含有三个连续的手性立体中心和两个连续的季螺构中心。反应在温和的反应条件下进行，无需任何催化剂，可产生高达55-99％的高区域和立体选择性产物。