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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
KeywordEmulsion Catalysis Asymmetric Catalysis Organocatalysis
Source PublicationCHINESE JOURNAL OF CHEMISTRY
2014-10-01
DOI10.1002/cjoc.201400431
Volume32Issue:10Pages:985-990
Indexed BySCI ; IC
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Multidisciplinary
WOS Research AreaChemistry
WOS KeywordASYMMETRIC ALDOL REACTIONS ; DIRECT SYN-ALDOL ; EMULSION DROPLETS ; ISOTETRONIC ACIDS ; MICHAEL ADDITION ; WATER ; ORGANOCATALYSTS ; CONSTRUCTION ; DIHYDROXYACETONE ; INTERFACE
AbstractA 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.
Language英语
WOS IDWOS:000343871100007
Citation statistics
Cited Times:4[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/145859
Collection中国科学院大连化学物理研究所
Affiliation1.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
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.
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