Construction of Bispirooxindole Heterocycles via Palladium-Catalyzed Ring-Opening Formal [3+2]-Cycloaddition of Spirovinylcyclopropyl Oxindole and 3-Oxindole Derivatives

被引：27

作者：

Xiao, Jun-An ^{[1
]}

Li, Yu-Chun ^{[1
]}

Luo, Zhi-Jin ^{[1
]}

Cheng, Xiu-Liang ^{[1
]}

Deng, Zhi-Xiong ^{[2
]}

Chen, Wen-Qiang ^{[1
]}

Su, Wei ^{[1
]}

Yang, Hua ^{[2
]}

机构：

[1] Nanning Normal Univ, Guangxi Key Lab Nat Polymer Chem & Phys, Nanning 530001, Peoples R China

[2] Cent S Univ, Coll Chem & Chem Engn, Changsha 410083, Hunan, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 04期

基金：

中国国家自然科学基金;

关键词：

DONOR-ACCEPTOR CYCLOPROPANE; DIELS-ALDER REACTIONS; 3+2 CYCLOADDITION; ENANTIOSELECTIVE CONSTRUCTION; DIASTEREOSELECTIVE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; VINYL CYCLOPROPANES; STEREOCENTERS; ISATINS;

D O I：

10.1021/acs.joc.8b02889

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed ring-opening oxo-formal [3 + 2]-cycloaddition reaction of novel donor-acceptor spirovinylcyclopropyl oxindole with 3-oxindole is described. The developed protocol provides facile access to oxo-bispirooxindole derivatives in good yields (up to 82% yield) with excellent diastereoselectivities (up to 20:1 dr).

引用

页码：2297 / 2306

页数：10

共 35 条

[1] Palladium-catalysed ring-opening [3+2]-annulation of spirovinylcyclopropyl oxindole to diastereoselectively access spirooxindoles
Xiao, Jun-An
Cheng, Xiu-Liang
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He, Yi-Miao
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Su, Wei
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[2] Palladium-catalyzed asymmetric [3+2] cycloaddition to construct 1,3-indandione and oxindole-fused spiropyrazolidine scaffolds
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[4] Diastereo- and Enantioselective Construction of Oxindole-Fused Spirotetrahydrofuran Scaffolds through Palladium-Catalyzed Asymmetric [3+2] Cycloaddition of Vinyl Cyclopropanes and Isatins
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