文献类型：期刊文献

英文题名：2-(Acetoxymethyl)buta-2,3-dienoate, a Versatile 1,4-Biselectrophile for Phosphine-Catalyzed (4+n) Annulations with 1,n-Bisnucleophiles (n=1, 2)

作者：Zhang, Qiongmei;Yang, Lei;Tong, Xiaofeng[1]

机构：[1]E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China; E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

年份：2010

卷号：132

期号：8

起止页码：2550

外文期刊名：JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000275117900030)，CCR-EXPANDED(收录号:WOS:000275117900030)】；

语种：英文

摘要：A novel PPh(3)-catalyzed (4 + n) annulation of 2-(acetoxymethyl)buta-2,3-dienoates 1c-c with 1,n-binucleophiles (n = 1, 2) has been developed to provide a facile synthetic method for cyclopentene and 1,2,3,6-tetrahydropyridazine derivatives. The acetate group of 2-(acetoxymethyl)buta-2,3-dienoate is crucial for the Formation of 1,4-biselectrophilic intermediate C, which is recognized to be a 1,4-biselectrophile that can react with 1,n-bisnucleophiles. Deuterium studies also suggest that the reaction pathway involves a proton-transfer process.