DICP OpenIR
Highly Enantioselective Reactions of Cyclohexanone and beta,gamma-Unsaturated alpha-Keto Ester: The Tuning of Chemo-selectivities by Secondary and Primary Amine Catalysts
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
2014-10-01
DOI10.1002/cjoc.201400431
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
关键词[WOS]ASYMMETRIC ALDOL REACTIONS ; DIRECT SYN-ALDOL ; EMULSION DROPLETS ; ISOTETRONIC ACIDS ; MICHAEL ADDITION ; WATER ; ORGANOCATALYSTS ; CONSTRUCTION ; DIHYDROXYACETONE ; INTERFACE
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.
语种英语
WOS记录号WOS:000343871100007
引用统计
文献类型期刊论文
条目标识符http://cas-ir.dicp.ac.cn/handle/321008/145859
专题中国科学院大连化学物理研究所
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
推荐引用方式
GB/T 7714
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.
APA Wei, Jianwei,Guo, Wengang,Zhou, Xin,Du, Xin,Liu, Yan,&Li, Can.(2014).Highly Enantioselective Reactions of Cyclohexanone and beta,gamma-Unsaturated alpha-Keto Ester: The Tuning of Chemo-selectivities by Secondary and Primary Amine Catalysts.CHINESE JOURNAL OF CHEMISTRY,32(10),985-990.
MLA Wei, Jianwei,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".CHINESE JOURNAL OF CHEMISTRY 32.10(2014):985-990.
条目包含的文件
条目无相关文件。
个性服务
推荐该条目
保存到收藏夹
查看访问统计
导出为Endnote文件
谷歌学术
谷歌学术中相似的文章
[Wei, Jianwei]的文章
[Guo, Wengang]的文章
[Zhou, Xin]的文章
百度学术
百度学术中相似的文章
[Wei, Jianwei]的文章
[Guo, Wengang]的文章
[Zhou, Xin]的文章
必应学术
必应学术中相似的文章
[Wei, Jianwei]的文章
[Guo, Wengang]的文章
[Zhou, Xin]的文章
相关权益政策
暂无数据
收藏/分享
所有评论 (0)
暂无评论
 

除非特别说明,本系统中所有内容都受版权保护,并保留所有权利。