Efficient Enantioselective Michael Addition of Nitroalkenes Catalyzed by a Surfactant-Type Bifunctional Thiourea Organocatalyst in the Presence of Water

被引：7
|
作者：
Li, Jian [2 ]
Liu, Yang [3 ]
Liu, Li [1 ]
机构：
[1] Chang Zhou Univ, Analyt Ctr, Changzhou 213164, Peoples R China
[2] Chang Zhou Univ, Sch Pharmaceut Engn & Life Sci, Changzhou 213164, Peoples R China
[3] Kaifeng Univ, Res Ctr Funct Mat, Kaifeng 475004, Peoples R China
来源：
LETTERS IN ORGANIC CHEMISTRY | 2012年 / 9卷 / 01期
关键词：
Bifunctional thiourea; enantioselective michael addition; organocatalysts; surfactant-type; water; DIRECT ALDOL REACTIONS; ALPHA; BETA-UNSATURATED IMIDES; ALDEHYDES; NITROSTYRENES; ACTIVATION; KETONES;
D O I：
10.2174/157017812799304024
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
New surfactant-type bifunctional thiourea organocatalysts 3 were synthesized. It was found that in the presence of 10 mol% PhCOOH, bifunctional thiourea bearing a long chain 3b in 10 mol% loading could smoothly catalyze the asymmetric Michael reaction of nitroalkenes 4 with cyclohexanone at room temperature in the presence of water, giving the desired adducts 5a-i in good yields (80 - 93%) with high diastereoselectivities (syn/anti = 95/5 - > 99/1) and enantioselectivities (up to 92% ee).
引用
收藏
页码：51 / 55
页数：5
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