文献类型：期刊文献

英文题名：Cinchona Alkaloid-Derived Thiourea-Catalyzed Diastereo- and Enantioselective [3+2]Cycloaddition Reaction of Isocyanoacetates to Isatins: A Facile Access to Optically Active Spirooxindole Oxazolines

作者：Zhao, Mei-Xin[1,2,3];Zhou, Hao[1,2];Tang, Wen-Hao[1,2];Qu, Wei-Song[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, CAS Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China;[4]Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

年份：2013

卷号：355

期号：7

起止页码：1277

外文期刊名：ADVANCED SYNTHESIS & CATALYSIS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000318762100008)，CCR-EXPANDED(收录号:WOS:000318762100008)】；

基金：We are grateful for financial support from the National Natural Science Foundation of China (20772030, 21072056, 21272067), the Fundamental Research Funds for the Central Universities, Scientific Research Foundation for the Returned Overseas Chinese Scholars, and State Education Ministry.

语种：英文

外文关键词：cycloaddition; isatins; isocyanoacetates; organocatalysis; spiro compounds; synthetic methods

摘要：An efficient diastereo- and enantioselective [3+2]cycloaddition reaction of -aryl isocyanoacetates to isatins catalyzed by a quinine-derived bifunctional amine-thiourea-bearing sulfonamide as multiple hydrogen-bonding donor catalyst has been investigated. The corresponding adducts, which bear a spirocyclic quaternary stereocenter at the C-3 position of the oxindole, were obtained in good yields (5195%), high diastereoselectivities (up to >20:1 dr) and good to excellent enantioselectivities (up to 97% ee).