A convenient method for synthesis of polyfunctional dihydropyrrole spiro-fused oxindole-2-ones via an organocatalytic tandem Michael/cyclization sequence

被引：16
|
作者：
Liu, Xiong-Wei [1 ]
Yang, Jun [1 ]
Yang, Chao [1 ]
Han, Wen-Yong [2 ]
Liu, Xiong-Li [1 ]
Zhou, Ying [1 ]
Yu, Zhang-Biao [1 ]
Yuan, Wei-Cheng [2 ]
机构：
[1] Guizhou Univ, Coll Pharm, Guizhou Engn Ctr Innovat Tradit Chinese Med & Eth, Guiyang 550025, Peoples R China
[2] Chinese Acad Sci, Chengdu Inst Organ Chem, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu 610041, Peoples R China
来源：
TETRAHEDRON LETTERS | 2014年 / 55卷 / 51期
基金：
中国国家自然科学基金;
关键词：
Spirocyclic oxindoles; Dihydropyrrole; Quaternary-tertiary stereocenters; Michael/cyclization; Organocatalysis; 3-ISOTHIOCYANATO OXINDOLES; HIGHLY EFFICIENT; STEREOSELECTIVE CONSTRUCTION; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; MICHAEL ADDITIONS; DIELS-ALDER; SPIROOXINDOLES; BEARING; HYDROXYLATION;
D O I：
10.1016/j.tetlet.2014.11.006
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new methodology was developed for the synthesis of spirocyclic oxindoles bearing polyfunctional dihydropyrrole units via an organocatalytic tandem Michaelicyclization sequence. Products bearing adjacent quaternary-tertiary stereocenters were smoothly obtained in high yields (up to 97% yield) with excellent diastereoselectivities up to >20/1. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7110 / 7113
页数：4
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