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题名: Highly Enantioselective Reactions of Cyclohexanone and beta,gamma-Unsaturated alpha-Keto Ester: The Tuning of Chemo-selectivities by Secondary and Primary Amine Catalysts
作者: Wei, Jianwei1, 2;  Guo, Wengang1;  Zhou, Xin1;  Du, Xin2;  Liu, Yan1;  Li, Can1
关键词: emulsion catalysis ;  asymmetric catalysis ;  organocatalysis
刊名: CHINESE JOURNAL OF CHEMISTRY
发表日期: 2014-10-01
DOI: 10.1002/cjoc.201400431
卷: 32, 期:10, 页:985-990
收录类别: SCI ;  IC
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Multidisciplinary
研究领域[WOS]: Chemistry
英文摘要: A series of of amphiphilic imidazole based secondary and primary amine catalysts were synthesized and shown to be very effective with an acid cocatalyst for the asymmetric reaction of cyclohexanone to ,-unsaturated -keto ester. Interestingly, primary and secondary amine catalysts show different regio-selectivities in this reaction. Under the catalysis of secondary amine 1, excellent enantioselectivities were observed for the products from direct 3+3 reactions of cyclohexanone with ,-unsaturated -keto esters using water as the solvent. Moreover, the same reactants catalyzed by the primary amines 2 lead to the aldol reactions, affording the corresponding products with high diastereoselectivities and up to 97% ee. Theoretical studies on the transition states by using a model in gas phase revealed that steric effect plays an important role on different chemo-selective induction between the secondary amine 1 and primary amine 2.
关键词[WOS]: ASYMMETRIC ALDOL REACTIONS ;  DIRECT SYN-ALDOL ;  EMULSION DROPLETS ;  ISOTETRONIC ACIDS ;  MICHAEL ADDITION ;  WATER ;  ORGANOCATALYSTS ;  CONSTRUCTION ;  DIHYDROXYACETONE ;  INTERFACE
语种: 英语
WOS记录号: WOS:000343871100007
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/145859
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Liaoning, Peoples R China
2.Dalian Univ Technol, Dept Chem, Dalian 116024, Liaoning, Peoples R China

Recommended Citation:
Wei, Jianwei,Guo, Wengang,Zhou, Xin,et al. Highly Enantioselective Reactions of Cyclohexanone and beta,gamma-Unsaturated alpha-Keto Ester: The Tuning of Chemo-selectivities by Secondary and Primary Amine Catalysts[J]. CHINESE JOURNAL OF CHEMISTRY,2014,32(10):985-990.
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