Highly Enantioselective Reactions of Cyclohexanone and beta,gamma-Unsaturated alpha-Keto Ester: The Tuning of Chemo-selectivities by Secondary and Primary Amine Catalysts
文献类型：期刊论文
| 作者 | Wei, Jianwei1,2; Guo, Wengang1; Zhou, Xin1; Du, Xin2; Liu, Yan1; Li, Can1 |
| 刊名 | chinese journal of chemistry
 |
| 出版日期 | 2014-10-01 |
| 卷号 | 32期号:10页码:985-990 |
| 关键词 | emulsion catalysis asymmetric catalysis organocatalysis |
| 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. |
| 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 |
| 收录类别 | SCI ; IC |
| 语种 | 英语 |
| WOS记录号 | WOS:000343871100007 |
| 公开日期 | 2016-05-09 |
| 源URL | [http://cas-ir.dicp.ac.cn/handle/321008/145859]  |
| 专题 | 大连化学物理研究所_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. |
入库方式： OAI收割
来源：大连化学物理研究所
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