Highly efficient construction of chiral dispirocyclic oxindole/thiobutyrolactam/chromanone complexes through Michael/cyclization cascade reactions with a rosin-based squaramide catalyst

被引：33

作者：

Lin, Ning ^{[1
,3
]}

Long, Xian-wen ^{[1
]}

Chen, Qing ^{[1
,3
]}

Zhu, Wen-run ^{[1
]}

Wang, Bi-chuan ^{[1
]}

Chen, Kai-bin ^{[1
]}

Jiang, Cai-wu ^{[1
]}

Weng, Jiang ^{[2
]}

Lu, Gui ^{[2
]}

机构：

[1] Guangxi Univ Chinese Med, Coll Pharm, Nanning 530200, Guangxi, Peoples R China

[2] Sun Yat Sen Univ, Sch Pharmaceut Sci, Inst Med Chem, Guangzhou 510006, Guangdong, Peoples R China

[3] Guangxi Zhuang Yao Med Ctr Engn & Technol, Nanning 530200, Guangxi, Peoples R China

来源：

TETRAHEDRON | 2018年 / 74卷 / 27期

基金：

中国国家自然科学基金;

关键词：

3-lsothiocyanato oxindoles; Chromanones; Dispirocyclic oxindoles; Asymmetric organocatalysis; Rosin-based squaramide catalyst; 3-ISOTHIOCYANATO OXINDOLES; ENANTIOSELECTIVE SYNTHESIS; BIFUNCTIONAL ORGANOCATALYSTS; CONJUGATE ADDITION; MICHAEL REACTION; STEREOCENTERS; SPIROOXINDOLES; DERIVATIVES; CYCLIZATION; SEQUENCE;

D O I：

10.1016/j.tet.2018.05.052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient asymmetric Michael/cyclization cascade reaction of 4-chromanones with isothiocyanato oxindoles has been revealed. Under bifunctional organocatalysis by rosin-based squaramide catalyst, a series of spiro[oxindole/thiobutyrolactamichromanone] complexes were conveniently constructed in a highly stereoselective manner (up to 99% yields, > 20:1 dr and >99% ee). The reaction leads to the formation of three contiguous stereogenic centers and two Spiro quaternary stereocenters. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：3734 / 3741

页数：8

共 2 条

[1] Highly efficient and diastereoselective construction of bispirooxindoles through a cascade Michael-cyclization reaction
Wu, Song
Zhu, Xingli
He, Wujun
Wang, Rongming
Xie, Xiaohua
Qin, Dabin
Jing, Linhai
Chen, Zeqin
TETRAHEDRON, 2013, 69 (52) : 11084 - 11091
[2] Highly Efficient Enantioselective Construction of Bispirooxindoles Containing Three Stereocenters through an Organocatalytic Cascade Michael-Cyclization Reaction
Wu, Hao
Zhang, Li-Li
Tian, Zhi-Qing
Huang, Yao-Dong
Wang, Yong-Mei
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (05) : 1747 - 1753

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