文献类型：期刊文献

英文题名：Diastereo- and enantioselective Mannich/cyclization cascade reaction of isocyanoacetates with cyclic sulfamide ketimines by cinchona alkaloid squaramide/AgOAc cooperative catalysis

作者：Zhao, Mei-Xin[1,2];Dong, Zhi-Wen[1,2];Zhu, Guang-Yu[1,2];Zhao, Xiao-Li[3];Shi, Min[1,2,4]

机构：[1]East China Univ Sci & Technol, Key Lab Adv Mat, 130 Mei Long Rd, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Inst Fine Chem, 130 Mei Long Rd, Shanghai 200237, Peoples R China;[3]East China Normal Univ, Dept Chem, 3663 N Zhongshan Rd, Shanghai 200062, Peoples R China;[4]Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai Inst Organ Chem, 354 Fenglin Rd, Shanghai 200032, Peoples R China

年份：2018

卷号：16

期号：25

起止页码：4641

外文期刊名：ORGANIC & BIOMOLECULAR CHEMISTRY

收录：;EI(收录号：20182705397846);WOS:【SCI-EXPANDED(收录号:WOS:000436517700008)，CCR-EXPANDED(收录号:WOS:000436517700008)】；

基金：We are grateful for financial support from the National Natural Science Foundation of China (21272067), the Natural Science Foundation of Shanghai (15ZR1411900), and the Fundamental Research Funds for the Central Universities (222201717003).

语种：英文

外文关键词：Organic compounds - Enantioselectivity - Alkaloids - Metabolites

摘要：We have developed an efficient diastereo- and enantioselective Mannich/cyclization cascade reaction of -substituted isocyanoacetates with 4-aryl-3-carbonyl-1,2,5-thiadiazole-1,1-dioxide type cyclic sulfamide ketimines cooperatively catalyzed by cinchona alkaloid-derived squaramide and AgOAc. The corresponding optically active 2,3,3a,4-tetrahydroimidazo[1,5-b][1,2,5]thiadiazole-1,1-dioxide derivatives were obtained in excellent yields (up to 99%) and good to excellent stereoselectivities (up to >20:1 dr, up to 94% ee).