Facile Synthesis of Spirooxindole-Cyclohexenes via Phosphine-Catalyzed [4+2] Annulation of α-Substituted Allenoates

被引：9
|
作者：
Chen, Rongshun [1 ]
Fan, Xia [2 ]
Xu, Zhaozhong [3 ,4 ]
He, Zhengjie [3 ,4 ]
机构：
[1] Nanjing Agr Univ, Jiangsu Key Lab Pesticide Sci, Coll Sci, Nanjing 210095, Jiangsu, Peoples R China
[2] Nanjing Agr Univ, Coll Food Sci & Technol, Nanjing 210095, Jiangsu, Peoples R China
[3] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
[4] Nankai Univ, Dept Chem, Tianjin 300071, Peoples R China
来源：
CHINESE JOURNAL OF CHEMISTRY | 2017年 / 35卷 / 09期
基金：
中国国家自然科学基金;
关键词：
4+2] annulation reaction; phosphine catalysis; spirocyclohexenes; allenoates; synthesis; 6-MEMBERED SPIROCYCLIC OXINDOLES; ELECTRON-DEFICIENT ALKENES; 3+2 CYCLOADDITION; ENANTIOSELECTIVE SYNTHESIS; ISATYLIDENE MALONONITRILES; 3,3'-SPIROCYCLIC OXINDOLES; MULTIPLE STEREOCENTERS; ASYMMETRIC-SYNTHESIS; CASCADE REACTION; DOMINO REACTION;
D O I：
10.1002/cjoc.201700112
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A phosphine-catalyzed [4+2] annulation of -substituted allenoate with exocyclic alkene moiety of oxindoles or indan-1,3-diones has been developed. Thus, under the catalysis of PPh3 (20mol%), a series of spirooxindole- or spiroindan-1,3-dione-cyclohexenes have been obtained in moderate to excellent yields and regioselectivity from the annulations of -methyl allenoates with 3-methyleneoxindoles or 2-methyleneindan-1,3-diones. This method offers an easy access to structurally novel spirocyclohexenes.
引用
收藏
页码：1469 / 1473
页数：5
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