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[1]; Yang, Lei[1]; Tong, Xiaofeng[1]

机构：[1] Key Laboratory for Advanced Materials, Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237, 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：EI(收录号：20101412827920)

语种：英文

外文关键词：Phosphorus compounds

摘要：(Figure Presented) A novel PPh3-catalyzed (4 + n) annulation of 2-(acetoxymethyl)buta-2,3-dienoates 1c-e with 1,n-bisnucleophiles (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. Copyright ? 2010 American Chemical Society.