Asymmetric Michael reaction of aldehydes with β-nitroalkenes catalyzed by pyrrolidine-camphor derived organocatalysts bearing hydrogen-bond donors

被引：7
|
作者：
Weng, Jiang [1 ]
Ai, Hui-Bing [1 ]
Luo, Ren-Shi [1 ]
Lu, Gui [1 ]
机构：
[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Inst Med Chem, Guangzhou 510006, Guangdong, Peoples R China
来源：
CHIRALITY | 2012年 / 24卷 / 04期
关键词：
asymmetric catalysis; organocatalysis; camphor; sulfonamide; Michael reaction; nitroalkene; aldehyde; hydrogen bond; ADDITIONS; KETONES;
D O I：
10.1002/chir.21991
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Several pyrrolidinecamphor derived organocatalysts were designed and synthesized. These organocatalysts were used for direct Michael reaction of aldehydes with nitroalkenes to give the desired ?-nitrocarbonyl compounds in high yields (up to 99%), high diastereoselectivities (syn:anti up to 92:8), and good to excellent enantioselectivities (up to 94% ee). Possible transition-state model was also proposed for this asymmetric transformation, which may involve hydrogen-bond interactions between the nucleophilic enamine formed in situ and the nitroalkenes. Chirality, 2012. (c) 2012 Wiley Periodicals, Inc.
引用
收藏
页码：271 / 275
页数：5
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