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手性N,N'-二氧化物/Cu(I)配合物催化的硝基烷烃与醛的催化不对称亨利反应。

Catalytic asymmetric Henry reaction of nitroalkanes and aldehydes catalyzed by a chiral N,N'-dioxide/Cu(I) complex.

作者信息

Mei Hongjiang, Xiao Xiao, Zhao Xiaohu, Fang Bing, Liu Xiaohua, Lin Lili, Feng Xiaoming

机构信息

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, People's Republic of China.

出版信息

J Org Chem. 2015 Feb 20;80(4):2272-80. doi: 10.1021/jo5027832. Epub 2015 Feb 10.

DOI:10.1021/jo5027832
PMID:25635710
Abstract

An easily available N,N'-dioxide/Cu(I) complex has been developed for the catalytic asymmetric nitroaldol (Henry) reaction of aldehydes with nitroethane. Under mild reaction conditions, a series of substituted aromatic, heteroaromatic and α,β-unsaturated aldehydes are transformed to the corresponding anti-β-nitroalcohols in good to excellent yields (up to 99%) with moderate to good dr (up to 16.7:1 anti/syn) and high ee values (up to 97%). Besides nitroethane, nitromethane and 1-nitropropane were also employed as nucleophiles, and good enantioselectivities were obtained.

摘要

一种易于获得的N,N'-二氧化物/Cu(I)配合物已被开发用于醛与硝基乙烷的催化不对称硝基羟醛（亨利）反应。在温和的反应条件下，一系列取代的芳香醛、杂芳香醛和α,β-不饱和醛以良好至优异的产率（高达99%）转化为相应的反-β-硝基醇，具有中等至良好的非对映选择性（高达16.7:1反/顺）和高对映体过量值（高达97%）。除了硝基乙烷，硝基甲烷和1-硝基丙烷也被用作亲核试剂，并获得了良好的对映选择性。

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引用本文的文献

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Copper-Catalyzed Propargylation of Nitroalkanes.铜催化的硝基烷烃的炔丙基化反应
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