Enantioselective Fluorination Reaction of β-Ketoester–Catalyzed Chiral Primary Amine–Based Multifunctional Catalyst Systems
文献类型：期刊论文
| 作者 | Shang, Jun-Yan1; Li L(李莉)1; Lu YX(卢一新)2,3; Yang KF(杨科芳)1; Xu LW(徐利文)1,4 |
| 刊名 | Synthetic Communications
 |
| 出版日期 | 2014 |
| 卷号 | 44期号:1页码:101-114 |
| 关键词 | Amino acid enantioselective fluorination Lewis acid organocatalysis primary amine |
| ISSN号 | 0039-7911 |
| 通讯作者 | 徐利文 |
| 英文摘要 | The fluorination reaction is an important organic transformation for asymmetric synthesis. In this article, we reported the determination of chiral primary amine–based multicatalyst systems for enantioselective fluorination of β-ketoester. Studies on the enantioselective organocatalytic fluorination promoted by cinchona alkaloid–derived chiral primary amines in the absence of various co catalysts revealed that the combined metal salts and organocatalysts resulted in poor conversion and enantioselectivities, whereas the combinational use of L-leucine and QN-NH2 as dual primary amine catalysts led to the determination of a novel dual organocatalyst with promising catalytic activity. On the basis of these results, we revealed that the steric environment of the chiral enamine intermediate formed by the condensation of β-ketoester with the chiral primary amine is most responsible for the observed enantioselectivity. |
| 学科主题 | 物理化学与绿色催化 |
| 收录类别 | SCI |
| 资助信息 | the National Natural Science Foundation of China (Nos. 20973051;21173064;51203037);Zhejiang Provincial Natural Science Foundation of China (Q12B020037);Education of Zhejiang Province (Y200803767);Program for Excellent Young Teacher in Hangzhou Normal University (HNUEYT, JTAS 2011-01-014) |
| 语种 | 英语 |
| WOS记录号 | WOS:000325514400010 |
| 源URL | [http://210.77.64.217/handle/362003/19284]  |
| 专题 | 兰州化学物理研究所_OSSO国家重点实验室 |
| 作者单位 | 1.Hangzhou Normal Univ, Minist Educ, Key Lab Organosilicon Chem & Mat Technol, Hangzhou, Zhejiang, Peoples R China 2.Natl Univ Singapore, Inst Life Sci, Dept Chem, Singapore 117548, Singapore 3.Natl Univ Singapore, Inst Life Sci, Med Chem Program, Singapore 117548, Singapore 4.Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China |
| 推荐引用方式 GB/T 7714 | Shang, Jun-Yan,Li L,Lu YX,et al. Enantioselective Fluorination Reaction of β-Ketoester–Catalyzed Chiral Primary Amine–Based Multifunctional Catalyst Systems[J]. Synthetic Communications,2014,44(1):101-114. |
| APA | Shang, Jun-Yan,Li L,Lu YX,Yang KF,&Xu LW.(2014).Enantioselective Fluorination Reaction of β-Ketoester–Catalyzed Chiral Primary Amine–Based Multifunctional Catalyst Systems.Synthetic Communications,44(1),101-114. |
| MLA | Shang, Jun-Yan,et al."Enantioselective Fluorination Reaction of β-Ketoester–Catalyzed Chiral Primary Amine–Based Multifunctional Catalyst Systems".Synthetic Communications 44.1(2014):101-114. |
入库方式： OAI收割
来源：兰州化学物理研究所
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