Formal [5+3] Cycloaddition of Vinylethylene Carbonates with Isatin-Based α-(Trifluoromethyl)imines for Diastereoselective Synthesis of Medium-Heterocycle-Fused Spirooxindoles

被引：34
|
作者：
Zhao, Hong-Wu [1 ]
Wang, Li-Ru [1 ]
Guo, Jia-Ming [1 ]
Ding, Wan-Qiu [1 ]
Song, Xiu-Qing [1 ]
Wu, Hui-Hui [1 ]
Tang, Zhe [1 ]
Fan, Xiao-Zu [1 ]
Bi, Xiao-Fan [1 ]
机构：
[1] Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2019年 / 361卷 / 20期
关键词：
5+3] cycloaddition; vinylethylene carbonate; isatin-based alpha-(trifluoromethyl)imine; spirooxindole; DECARBOXYLATIVE CYCLOADDITION; ENANTIOSELECTIVE CONSTRUCTION; 1,3-DIPOLAR CYCLOADDITION; PALLADIUM; BOND;
D O I：
10.1002/adsc.201900651
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
In the presence of Pd(PPh3)(4) (2.5 mol%), PPh3 (10 mol%) and pyridine (2.0 equiv.), the formal [5+3] cycloaddition of vinylethylene carbonates with isatin-based alpha-(trifluoromethyl)imines proceeded readily, and delivered trans-configured novelmedium-heterocycle-fused spirooxindoles in 75-97% chemical yields with excellent diastereoselectivities. The relative stereochemical configuration of the title products was identified by X-ray diffraction analysis.
引用
收藏
页码：4761 / 4771
页数：11
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