文献类型：期刊文献

英文题名：Cinchona Alkaloid Squaramide-Catalyzed Asymmetric Michael Addition of α-Aryl Isocyanoacetates to β-Trifluoromethylated Enones and Its Applications in the Synthesis of Chiral β-Trifluoromethylated Pyrrolines

作者：Zhao, Mei-Xin[1,2,3];Zhu, Hui-Kai[1,2];Dai, Tong-Lei[1,2];Shi, Min[1,2,4]

机构：[1]E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China;[2]E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China;[3]Chinese Acad Sci, Inst Chem, Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China;[4]Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

年份：2015

卷号：80

期号：22

起止页码：11330

外文期刊名：JOURNAL OF ORGANIC CHEMISTRY

收录：;EI(收录号：20154801621201);WOS:【SCI-EXPANDED(收录号:WOS:000365462600012)，CCR-EXPANDED(收录号:WOS:000365462600012)】；

基金：We are grateful for financial support from the National Natural Science Foundation of China (21072056, 21272067).

语种：英文

外文关键词：Carboxylation - Addition reactions - Alkaloids - Carbon - Metabolites

摘要：Cinchona alkaloid squaramide can effectively catalyze the asymmetric Michael addition of alpha-aryl isocyanoacetates to beta-trifluoromethylated enones, affording the corresponding adducts, with an adjacent chiral tertiary carbon center bearing a CF3 group and a quaternary carbon center in moderate to good yields along with excellent stereo-selectivities. The adduct can be easily transformed into biologically attractive chiral beta-trifluoromethylated pyrroline carboxylate in high yield via an isocyano group hydrolysis/cyclization/dehydration cascade reaction by treating with acid. The one-pot enantioselective Michael addition/isocyano group hydrolysis/cyclization/dehydration sequential protocol has also been investigated.