Diastereo- and Enantioselective Synthesis of Spiro-Pyrrolidine-Pyrazolones by Squaramide-Catalyzed Cascade Aza-Michael/Michael Reactions

被引：55
作者：
Li, Jun-Hua [1 ]
Wen, Hongliang [1 ]
Liu, Lei [1 ]
Du, Da-Ming [1 ]
机构：
[1] Beijing Inst Technol, Sch Chem Engn & Environm, 5 South Zhongguancun St, Beijing 100081, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 14期
基金：
中国国家自然科学基金;
关键词：
Asymmetric synthesis; Organocatalysis; Domino reactions; Michael addition; Spiro compounds; Nitrogen heterocycles; ORGANOCATALYTIC DOMINO REACTIONS; ASYMMETRIC-SYNTHESIS; BIOLOGICAL-ACTIVITY; EFFICIENT SYNTHESIS; TRISUBSTITUTED PYRROLIDINES; 3-ISOTHIOCYANATO OXINDOLES; UNSATURATED PYRAZOLONES; CHIRAL SQUARAMIDE; MICHAEL ADDITION; DERIVATIVES;
D O I：
10.1002/ejoc.201600316
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new method was developed to rapidly generate a series of spiro-pyrrolidine-pyrazolones by using a squaramide-catalyzed cascade aza-Michael/Michael addition of either tosyl-aminomethyl enones or enoates to unsaturated pyrazolones. This tandem reaction sequence proceeded well by using 5 mol-% of a chiral bifunctional tertiary amine squaramide catalyst to afford the desired products in good to excellent yields (up to 98 %) with excellent diastereoselectivities [up to >20:1 diastereomeric ratio (dr)] and high to excellent enantioselectivities (up to 98 % ee).
引用
收藏
页码：2492 / 2499
页数：8
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