手性磷酸催化芳香胺与硝基烯烃的不对称加成反应

催化学报 ›› 2011, Vol. 32 ›› Issue (10): 1573-1576.

手性磷酸催化芳香胺与硝基烯烃的不对称加成反应

杨磊, 夏春谷, 黄汉民*

中国科学院兰州化学物理研究所羰基合成与选择氧化国家重点实验室, 甘肃兰州 730000

收稿日期:2011-07-07 修回日期:2011-08-06 出版日期:2011-09-30 发布日期:2015-02-12

Chiral Phosphoric Acid Catalyzed Enantioselective Aza-Michael Addition of Aromatic Amines to Nitroolefins

YANG Lei, XIA Chungu, HUANG Hanmin*

State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, Gansu, China

Received:2011-07-07 Revised:2011-08-06 Online:2011-09-30 Published:2015-02-12

摘要/Abstract

摘要： 以轴手性联萘酚为原料, 合成了一系列手性磷酸催化剂, 并首次将其应用于催化芳香胺和硝基烯烃的不对称氮杂迈克尔加成反应中, 产物 β-硝基胺的产率和对映选择性分别达 65%~95% 和 16%~70%.

关键词: 手性磷酸, 芳香胺, 硝基烯烃, 氮杂迈克尔加成

Abstract: Chiral phosphoric acid was found to be an effective organocatalyst in the enantioselective aza-Michael addition of aromatic amines to nitroolefins giving the corresponding β-nitroamine products in good yields (65%–95%) with moderate to good enantiomeric excesses (16%–70%). This study represents the first example of a chiral phosphoric acid catalyzed asymmetric aza-Michael addition reaction.

Key words: chiral phosphoric acid, aromatic amine, nitroolefin, aza-Michael addition

杨磊, 夏春谷, 黄汉民. 手性磷酸催化芳香胺与硝基烯烃的不对称加成反应[J]. 催化学报, 2011, 32(10): 1573-1576.

YANG Lei, XIA Chun-Gu, HUANG Han-Min. Chiral Phosphoric Acid Catalyzed Enantioselective Aza-Michael Addition of Aromatic Amines to Nitroolefins[J]. Chinese Journal of Catalysis, 2011, 32(10): 1573-1576.

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