ICCAS OpenIR
Asymmetric Michael addition of aldehydes to nitroolefins catalyzed by L-prolinamide derivatives using phenols as co-catalysts
Cheng, Yan-Qin; Bian, Zheng; He, Ya-Bing; Han, Fu-She; Kang, Chuan-Qing; Ning, Zhao-Lun; Gao, Lian-Xun
2009-08-12
Source PublicationTETRAHEDRON-ASYMMETRY
ISSN0957-4166
Volume20Issue:15Pages:1753-1758
AbstractThe asymmetric Michael addition of aldehydes to nitroolefins was investigated using L-prolinamide derivatives of 2-(2'-piperidinyl)pyridine as catalyst and a variety of phenols as co-catalyst. Extensive screening toward the effect of prolinamides, phenols, and solvents on this transformation revealed that a combination of (S)-2-(2'-piperidinyl)pyridine-derived trans-4-hydroxy-L-prolinamide 2c, (S)-1,1'-bi-2-naphthol, and dichloromethane was a promising system. This system was shown to be amenable to a rich variety of aldehydes and nitroolefins and afforded the nitroaldehyde products with excellent yield, enantiomeric excess (up to 99%) and diastereoselectivity ratio (up to 99/1), even in the case of 1 mol % catalyst loading and 1.5 equiv of aldehydes. (c) 2009 Elsevier Ltd. All rights reserved.
DOI10.1016/j.tetasy.2009.07.022
Indexed BySCI ; IC ; CCR
Language英语
WOS IDWOS:000270126100010
PublisherPERGAMON-ELSEVIER SCIENCE LTD
Citation statistics
Cited Times:12[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/66370
Collection中国科学院化学研究所
Corresponding AuthorGao, Lian-Xun
AffiliationChinese Acad Sci, Changchun Inst Appl Chem, Grad Sch, State Key Lab Polymer Phys & Chem, Changchun 130022, Peoples R China
Recommended Citation
GB/T 7714
Cheng, Yan-Qin,Bian, Zheng,He, Ya-Bing,et al. Asymmetric Michael addition of aldehydes to nitroolefins catalyzed by L-prolinamide derivatives using phenols as co-catalysts[J]. TETRAHEDRON-ASYMMETRY,2009,20(15):1753-1758.
APA Cheng, Yan-Qin.,Bian, Zheng.,He, Ya-Bing.,Han, Fu-She.,Kang, Chuan-Qing.,...&Gao, Lian-Xun.(2009).Asymmetric Michael addition of aldehydes to nitroolefins catalyzed by L-prolinamide derivatives using phenols as co-catalysts.TETRAHEDRON-ASYMMETRY,20(15),1753-1758.
MLA Cheng, Yan-Qin,et al."Asymmetric Michael addition of aldehydes to nitroolefins catalyzed by L-prolinamide derivatives using phenols as co-catalysts".TETRAHEDRON-ASYMMETRY 20.15(2009):1753-1758.
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