Recyclable copper catalysts based on ionic-tagged C2-symmetric Indabox ligands and their application in asymmetric Henry reactions

被引：19
作者：
Li, Zhi-Huai [1 ]
Zhou, Zhi-Ming [1 ,2 ]
Hao, Xiao-Yan [1 ]
Zhang, Jun [1 ]
Dong, Xiao [1 ]
Liu, Ying-Qiang [1 ]
Sun, Wen-Wen [1 ]
Cao, Dan [1 ]
机构：
[1] Beijing Inst Technol, Sch Chem Engn & Environm, R&D Ctr Pharmaceut, Beijing 100081, Peoples R China
[2] Beijing Inst Technol, State Key Lab Explos Sci & Technol, Beijing 100081, Peoples R China
来源：
APPLIED CATALYSIS A-GENERAL | 2012年 / 425卷
关键词：
Catalyst recycled; Imidazolium/pyrrolidinium-tagged; Indabox; Asymmetric Henry reaction; Theoretical mechanistic study; OXAZOLINE-CONTAINING LIGANDS; SALEN-CHROMIUM COMPLEXES; NITROALDOL REACTION; BIS(OXAZOLINE)-COPPER COMPLEXES; LIQUIDS; SILICA; ENANTIOSELECTIVITY; CYCLOPROPANATION; IMMOBILIZATION; FACILE;
D O I：
10.1016/j.apcata.2012.02.044
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
New imidazolium/pyrrolidinium-tagged Indabox ligands were designed and prepared. Catalysts based on these ligands with Cu(OAc)(2)center dot H2O were applied to the asymmetric Henry reaction using various aldehydes and CH3NO2, the products were obtained in high enantioselectivity. Specifically, (R)-1-(2-methoxylphenyl)-2-nitroethanol was obtained in 94% ee in MeOH. Furthermore, the catalyst based on 7 could be recycled at least 12 times by simple wash without an obvious loss of activity or enantioselectivity. This catalytic procedure demonstrated the potential for catalyst recyclability in the asymmetric Henry reaction. Additionally, a theoretical mechanistic study was conducted to explain the origin of the enantioselectivity. (C) 2012 Elsevier B.V. All rights reserved.
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收藏
页码：28 / 34
页数：7
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