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双核锌-氮杂苯并菲催化 Boc 保护的亚胺和硝基烷烃在温和条件下的不对称氮杂 Henry 反应。

Dinuclear Zinc-AzePhenol Catalyzed Asymmetric Aza-Henry Reaction of N-Boc Imines and Nitroalkanes under Ambient Conditions.

机构信息

Shaanxi Key Laboratory of Chemical Additives for Industry, College of Chemistry and Chemical Engineering , Shaanxi University of Science and Technology , 6 Xuefu Road , Weiyang District, Xi'an , Shaanxi 710021 , P. R. China.

College of Chemistry and Pharmaceutical Engineering , Nanyang Normal University , 1638 Wolong Road , Nanyang , Henan 473061 , P. R. China.

出版信息

J Org Chem. 2019 Mar 1;84(5):2652-2659. doi: 10.1021/acs.joc.8b02943. Epub 2019 Feb 15.

Abstract

The asymmetric aza-Henry reaction of N-Boc imines and nitroalkanes was realized in the presence of 10 mol % dinuclear zinc-AzePhenol catalysts under ambient conditions. A variety of nitroamines were obtained in good yields (up to 97%) with excellent enantioselectivities (up to 99% ee) and high diasteroselectivity (up to 14:1 dr). Our protocol combined the operational simplicity and mild reaction conditions, thus making the process amenable for technical applications.

摘要

在环境条件下,使用 10 mol%双核锌-AzePhenol 催化剂实现了 N-Boc 亚胺和硝基烷烃的不对称氮杂 Henry 反应。多种硝基胺以良好的收率(高达 97%)和优异的对映选择性(高达 99%ee)和高非对映选择性(高达 14:1dr)获得。我们的方案结合了操作简单和温和的反应条件,因此使该过程适用于技术应用。

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