Phosphine-Catalyzed Annulations between Modified Allylic Derivatives and Polar Dienes and Substituent Effect on the Annulation Mode  

作　　者：Junjun Tian Haiyun Sun Rong Zhou Zhengjie He 

机构地区：[1]State Key Laboratory of Elemento-Organic Chemistry, Synergetic Innovation Center of Chemical Science and Engineering ( Tianjin), and Department of Chemistry, Nankai Universi~, Tianjin 300071, China

出　　处：《Chinese Journal of Chemistry》2013年第10期1348-1351,共4页中国化学（英文版）

基　　金：Acknowledgement Financial support from National Natural Science Foundation of China （Nos. 21072100; 21121002; 21272119） is gratefully acknowledged.

摘　　要：in this work, the phosphine-catalyzed annulation reactions between modified allylic derivatives and polar 1,1-dicyano-1,3-dienes have been studied. In the catalysis of PPh3 （20 mol%）, a [4 ＋ 1 ] annulation reaction is realized between a series of l,l-dicyano-2,4-diaryl-1,3-dienes and ethoxycarbonyl-activated allylic acetate, producing polysubstituted cyclopentenes in modest to excellent yields. It is also observed that the substituents of both 1,3-dienes and allylic derivatives have a significant influence on the annulation mode： under the catalysis of PPh3 or PBu3 （20 mol%）, regioselective [3 ＋ 2] annulation products are formed from differently substituted substratcs.in this work, the phosphine-catalyzed annulation reactions between modified allylic derivatives and polar 1,1-dicyano-1,3-dienes have been studied. In the catalysis of PPh3 （20 mol%）, a [4 ＋ 1 ] annulation reaction is realized between a series of l,l-dicyano-2,4-diaryl-1,3-dienes and ethoxycarbonyl-activated allylic acetate, producing polysubstituted cyclopentenes in modest to excellent yields. It is also observed that the substituents of both 1,3-dienes and allylic derivatives have a significant influence on the annulation mode： under the catalysis of PPh3 or PBu3 （20 mol%）, regioselective [3 ＋ 2] annulation products are formed from differently substituted substratcs.

关 键 词：[4＋ 1 ] annulation reaction [3 ＋2] annulation reaction phosphine catalysis CYCLOPENTENES DIENES 

分 类 号：O626.13[理学—有机化学] TQ655[理学—化学]