Facile Synthesis of Spirooxindole-Cyclohexenes via Phosphine-Catalyzed [4-1-2] Annulation of α-Substituted Allenoates  

作　　者：Rongshun Chen Xia Fan Zhaozhong Xu Zhengjie He 

机构地区：[1]Jiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing, Jiangsu 210095, China [2]College of Food Science and Technology, Nanjing Agricultural University, Nanjing, Jiangsu 210095, China [3]The State Key Laboratory of Elemento-Organic Chemistry and Department of Chemistry, Nankai University, Tianjin 300071, China

出　　处：《Chinese Journal of Chemistry》2017年第9期1469-1473,共5页中国化学（英文版）

基　　金：Financial support from the Fundamental Research Funds for the Central Universities （No. KYZ201749） and the National Natural Science Foundation of China （Nos. 21272119, J1103306） are gratefully acknowledged.

摘　　要：A phosphine-catalyzed [4＋2] annulation of a-substituted allenoate with exocyclic alkene moiety of oxindoles or indan-1,3-diones has been developed. Thus, under the catalysis of PPh3 （20 mol%）, a series of spirooxindole- or spiroindan-1,3-dione-cyclohexenes have been obtained in moderate to excellent yields and regioselectivity from the annulations of a-methyl allenoates with 3-methyleneoxindoles or 2-methyleneindan-1,3-diones. This method offers an easy access to structurally novel spirocyclohexenes.A phosphine-catalyzed [4＋2] annulation of a-substituted allenoate with exocyclic alkene moiety of oxindoles or indan-1,3-diones has been developed. Thus, under the catalysis of PPh3 （20 mol%）, a series of spirooxindole- or spiroindan-1,3-dione-cyclohexenes have been obtained in moderate to excellent yields and regioselectivity from the annulations of a-methyl allenoates with 3-methyleneoxindoles or 2-methyleneindan-1,3-diones. This method offers an easy access to structurally novel spirocyclohexenes.

关 键 词：[4＋2] annulation reaction phosphine catalysis spirocyclohexenes ALLENOATES synthesis 

分 类 号：O626.13[理学—有机化学] TQ265.1[理学—化学]