Temperature-Dependent Cinchona Alkaloid Squaramide-Catalyzed Asymmetric Formal [3+2] Cycloaddition of Isocyanoacetates with -Trifluoromethylated Enones

被引：16
|
作者：
Zhao, Mei-Xin [1 ,2 ]
Zhu, Guang-Yu [1 ,2 ]
Zhu, Hui-Kai [1 ,2 ]
Zhao, Xiao-Li [3 ]
Ji, Ming [1 ,2 ]
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, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 354 Fenglin Rd, Shanghai 200032, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 29期
基金：
上海市自然科学基金; 中国国家自然科学基金;
关键词：
Organocatalysis; Cycloaddition; Isocyanoacetates; Enones; Pyrroles; ALPHA-SUBSTITUTED ISOCYANOACETATES; ENANTIOSELECTIVE MICHAEL ADDITION; MANNICH-TYPE REACTION; ALDOL REACTION; ARYL ISOCYANOESTERS; N-SULFONYLIMINES; CASCADE REACTION; CYCLIZATION; ACCESS; ESTERS;
D O I：
10.1002/ejoc.201800511
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient temperature-dependent organocatalyzed asymmetric formal [3+2] cycloaddition reaction of -substituted isocyanoacetates to -trifluoromethylated enones by cinchona alkaloid-derived squaramide has been investigated, affording the optically active trifluoromethylated 2-pyrrolines in excellent yields (up to 98%) and high stereoselectivities (>20:1 dr, up to >99% ee) under mild conditions.
引用
收藏
页码：3997 / 4005
页数：9
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