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通过 3-苯甲酰基氧化吲哚的自串联 Michael-aldol 反应构建双螺环戊二烯并双氧吲哚。

Construction of dispirocyclopentanebisoxindoles via self-domino Michael-aldol reactions of 3-phenacylideneoxindoles.

机构信息

College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China.

出版信息

J Org Chem. 2013 Sep 6;78(17):8354-65. doi: 10.1021/jo4010603. Epub 2013 Aug 26.

Abstract

A simple protocol for the construction of novel dispirocyclopentanebisoxindoles is accomplished by the base promoted domino reactions between two molecules of 3-phenacylideneoxindoles with the participation of solvents, alcohol, or other added nucleophiles such as amines or thiophenols. Significantly, this domino reaction results in the complex dispiro compounds with high yields and diastereoselectivity, which would allow construction of dispirocyclopentanebisoxindole with four and five diastereoisomeric centers using simple materials.

摘要

通过两个 3-苯甲酰基氧吲哚分子在碱促进下与溶剂、醇或其他亲核试剂(如胺或硫酚)参与的多米诺反应,完成了新型双螺环戊烷双氧吲哚的简单构建。值得注意的是,这种多米诺反应导致复杂的双螺化合物具有高产率和立体选择性,这使得使用简单的材料可以构建具有四个和五个非对映异构中心的双螺环戊烷双氧吲哚。

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