文献类型：期刊文献

英文题名：Chiral amine-catalyzed enantioselective cascade aza-ene-type cyclization reactions

作者：Zu, Liansuo[2];Xie, Hexin[2];Li, Hao[2];Wang, Jian[2];Yu, Xinhong[1];Wang, Wei[1,2]

机构：[1]E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China;[2]Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA

年份：2008

卷号：14

期号：21

起止页码：6333

外文期刊名：CHEMISTRY-A EUROPEAN JOURNAL

收录：;EI(收录号：20144300128411);WOS:【SCI-EXPANDED(收录号:WOS:000258092400007)，CCR-EXPANDED(收录号:WOS:000258092400007)】；

语种：英文

外文关键词：aldehydes; cascade reactions; enamides; organocatalysis

摘要：A study was conducted to analyze the organocatalytic highly enantioselective cascade anaene-type cyclization reaction. The study is based on a hypothesis that a chiral secondary amine activated enal enabled a nucleophilic attack by enamide to produce intermediate enamine/iminium. The study found that the reaction of trans-4-nitrocinnamaldehyde with enamide and an organic catalyst, depend on the organocatalysts and additives. The study also found that a base additive can activate the enamide through deprotation and catalysis reaction by readily (S)-diphenylprolinol-TMS ether can establish multistep iminium/enamine transformation in one-pot operation. The study also observed that electronic and steric nature of the aryl rings of enals has limited impact on the stereochemical outcome.