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用于非对映选择性合成蝴蝶形双螺[氧化吲哚-吡咯烷]的伪五组分反应。

Pseudo-Five-Component Reaction for Diastereoselective Synthesis of Butterfly Shaped Bispiro[Oxindole-Pyrrolidine]s.

作者信息

Zhang Xiaofeng, Qiu Weiqi, Murray Stephanie A, Zhan Desheng, Evans Jason, Jasinski Jerry P, Wang Xiao, Zhang Wei

机构信息

Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, Massachusetts 02125, United States.

Department of Cancer Biology, Dana-Farber Cancer Institute, Boston, Massachusetts 02215, United States.

出版信息

J Org Chem. 2021 Dec 3;86(23):17395-17403. doi: 10.1021/acs.joc.1c01797. Epub 2021 Nov 19.

DOI:10.1021/acs.joc.1c01797
PMID:34797667
Abstract

A pseudo-five-component reaction involving double decarboxylative 1,3-dipolar cycloaddition of azomethine ylides with olefinic oxindoles for the diastereoselective synthesis of bispiro[oxindole-pyrrolidine]s is developed. The major diastereomers are unique butterfly shaped compounds with a plane of symmetry. Recyclable zeolite HY acid catalyst is used to promote the reaction, and only CO and HO are generated as byproducts.

摘要

开发了一种涉及甲亚胺叶立德与烯基氧化吲哚的双脱羧1,3-偶极环加成反应的伪五组分反应，用于非对映选择性合成双螺[氧化吲哚-吡咯烷]。主要非对映异构体是具有对称平面的独特蝴蝶形化合物。使用可回收的HY沸石酸催化剂促进反应，仅生成CO和HO作为副产物。

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