Asymmetric Michael addition of aldehydes to nitroolefins catalyzed by L-prolinamide derivatives using phenols as co-catalysts

doi:10.1016/j.tetasy.2009.07.022

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	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
刊名	TETRAHEDRON-ASYMMETRY
	2009-08-12
卷号	20 期号:15 页码:1753-1758
ISSN号	0957-4166
DOI	10.1016/j.tetasy.2009.07.022
英文摘要	The 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.
语种	英语
出版者	PERGAMON-ELSEVIER SCIENCE LTD
WOS记录号	WOS:000270126100010
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/66369]
专题	中国科学院化学研究所
通讯作者	Gao, Lian-Xun
作者单位	Chinese Acad Sci, Changchun Inst Appl Chem, Grad Sch, State Key Lab Polymer Phys & Chem, Changchun 130022, Peoples R China
推荐引用方式 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.