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DOI | 10.1126/science.aar7941 |
Asymmetric nucleophilic fluorination under hydrogen bonding phase-transfer catalysis | |
Pupo, Gabriele1; Ibba, Francesco1; Ascough, David M. H.1; Vicini, Anna Chiara1; Ricci, Paolo1; Christensen, Kirsten E.1; Pfeifer, Lukas1; Morphy, John Richard2; Brown, John M.1; Paton, Robert S.1; Gouverneur, Veronique1 | |
2018-05-11 | |
发表期刊 | SCIENCE
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ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2018 |
卷号 | 360期号:6389页码:638-+ |
文章类型 | Article |
语种 | 英语 |
国家 | England |
英文摘要 | Common anionic nucleophiles such as those derived from inorganic salts have not been used for enantioselective catalysis because of their insolubility. Here, we report that merging hydrogen bonding and phase-transfer catalysis provides an effective mode of activation for nucleophiles that are insoluble in organic solvents. This catalytic manifold relies on hydrogen bonding complexation to render nucleophiles soluble and reactive, while simultaneously inducing asymmetry in the ensuing transformation. We demonstrate the concept using a chiral bis-urea catalyst to form a tridentate hydrogen bonding complex with fluoride from its cesium salt, thereby enabling highly efficient enantioselective ring opening of episulfonium ion. This fluorination method is synthetically valuable considering the scarcity of alternative protocols and points the way to wider application of the catalytic approach with diverse anionic nucleophiles. |
领域 | 地球科学 ; 气候变化 ; 资源环境 |
收录类别 | SCI-E |
WOS记录号 | WOS:000431790900041 |
WOS关键词 | ENANTIOSELECTIVE FLUORINATION ; ENZYMATIC FLUORINATION ; FLUORIDE ; MECHANISM ; REACTIVITY ; CHEMISTRY ; EPOXIDES ; MOLECULE ; COMPLEX ; SYSTEM |
WOS类目 | Multidisciplinary Sciences |
WOS研究方向 | Science & Technology - Other Topics |
引用统计 | |
文献类型 | 期刊论文 |
条目标识符 | http://119.78.100.173/C666/handle/2XK7JSWQ/198620 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | 1.Univ Oxford, Chem Res Lab, 12 Mansfield Rd, Oxford OX1 3TA, England; 2.Eli Lilly & Co Ltd, Med Chem, Sunninghill Rd, Windlesham GU20 6PH, Surrey, England |
推荐引用方式 GB/T 7714 | Pupo, Gabriele,Ibba, Francesco,Ascough, David M. H.,et al. Asymmetric nucleophilic fluorination under hydrogen bonding phase-transfer catalysis[J]. SCIENCE,2018,360(6389):638-+. |
APA | Pupo, Gabriele.,Ibba, Francesco.,Ascough, David M. H..,Vicini, Anna Chiara.,Ricci, Paolo.,...&Gouverneur, Veronique.(2018).Asymmetric nucleophilic fluorination under hydrogen bonding phase-transfer catalysis.SCIENCE,360(6389),638-+. |
MLA | Pupo, Gabriele,et al."Asymmetric nucleophilic fluorination under hydrogen bonding phase-transfer catalysis".SCIENCE 360.6389(2018):638-+. |
条目包含的文件 | 条目无相关文件。 |
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