Divergent Synthesis of Multisubstituted Tetrahydrofurans and Pyrrolidines via Intramolecular Aldol-type Trapping of Onium Ylide Intermediates
文献类型：期刊论文
| 作者 | Jing, Changcheng1; Xing, Dong1; Gao, Lixin2; Li, Jia2 ; Hu, Wenhao1
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| 刊名 | CHEMISTRY-A EUROPEAN JOURNAL
 |
| 出版日期 | 2015-12-21 |
| 卷号 | 21期号:52页码:19202-19207 |
| 关键词 | diazo compounds heterocycles hydrogen bonds rhodium ylides |
| ISSN号 | 0947-6539 |
| DOI | 10.1002/chem.201503621 |
| 文献子类 | Article |
| 英文摘要 | This paper reports a divergent strategy for the synthesis of multisubstituted tetrahydrofurans and pyrrolidines, starting from easily accessible beta-hydroxyketones or beta-aminoketones to react with diazo compounds. Under Rh-II catalysis, this transformation is proposed to proceed through a metal-carbene-induced oxonium ylide or ammonium ylide formation followed by an intramolecular aldol-type trapping of these active intermediates. A series of highly substituted tetrahydrofurans and pyrrolidines are synthesized in high yields with good to excellent diastereoselectivities. Preliminary biological evaluations revealed that both types of heterocycles show good PTP1B inhibitory activities. |
| WOS关键词 | PROTEIN-TYROSINE PHOSPHATASES ; ENANTIOSELECTIVE 3-COMPONENT REACTIONS ; STEREOSELECTIVE-SYNTHESIS ; DIAZO-COMPOUNDS ; DIASTEREOSELECTIVE SYNTHESIS ; CYCLOADDITION REACTIONS ; AZOMETHINE YLIDES ; AMMONIUM YLIDES ; CATALYZED CARBOETHERIFICATION ; SUBSTITUTED TETRAHYDROFURANS |
| 资助项目 | NSF of China[21125209] ; NSF of China[21332003] ; NSF of China[21402051] ; MOST of China[2011CB808600] ; STCSM[12JC1403800] ; Scholarship Award for Excellent Doctoral Student - East China Normal University[XRZZ2013021] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000368282100045 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/276281]  |
| 专题 | 国家新药筛选中心 中科院受体结构与功能重点实验室 新药研究国家重点实验室 药物安全性评价中心 |
| 通讯作者 | Xing, Dong |
| 作者单位 | 1.E China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, Shanghai 200062, Peoples R China; 2.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Chinese Natl Ctr Drug Screening, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Jing, Changcheng,Xing, Dong,Gao, Lixin,et al. Divergent Synthesis of Multisubstituted Tetrahydrofurans and Pyrrolidines via Intramolecular Aldol-type Trapping of Onium Ylide Intermediates[J]. CHEMISTRY-A EUROPEAN JOURNAL,2015,21(52):19202-19207. |
| APA | Jing, Changcheng,Xing, Dong,Gao, Lixin,Li, Jia,&Hu, Wenhao.(2015).Divergent Synthesis of Multisubstituted Tetrahydrofurans and Pyrrolidines via Intramolecular Aldol-type Trapping of Onium Ylide Intermediates.CHEMISTRY-A EUROPEAN JOURNAL,21(52),19202-19207. |
| MLA | Jing, Changcheng,et al."Divergent Synthesis of Multisubstituted Tetrahydrofurans and Pyrrolidines via Intramolecular Aldol-type Trapping of Onium Ylide Intermediates".CHEMISTRY-A EUROPEAN JOURNAL 21.52(2015):19202-19207. |
入库方式： OAI收割
来源：上海药物研究所
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