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题名: Enantioselective Synthesis of Highly Functionalized Dihydrofurans through Copper-Catalyzed Asymmetric Formal [3+2] Cycloaddition of beta-Ketoesters with Propargylic Esters
作者: Zhu, Fu-Lin1, 2;  Wang, Ya-Hui1;  Zhang, De-Yang1, 2;  Xu, Jie1;  Hu, Xiang-Ping1
关键词: 2,3-dihydrofurans ;  asymmetric catalysis ;  copper ;  cycloadditions ;  synthetic methods
刊名: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
发表日期: 2014-09-15
DOI: 10.1002/anie.201405857
卷: 53, 期:38, 页:10223-10227
收录类别: SCI ;  IC ;  CCR
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Multidisciplinary
研究领域[WOS]: Chemistry
英文摘要: An enantioselective synthesis of highly functionalized dihydrofurans through a copper-catalyzed asymmetric [3+2] cycloaddition of beta-ketoesters with propargylic esters has been developed. With a combination of Cu(OTf)(2) and a chiral tridentate P, N, N ligand as the catalyst, a variety of 2,3-dihydrofurans bearing an exocyclic double bond at the 2 position were obtained in good chemical yields and with good to high enantioselectivities. The exocyclic double bond can be hydrogenated in a highly diastereoselective fashion to give unusual cis-2,3-dihydrofuran derivatives, thus further enhancing the scope of this transformation.
关键词[WOS]: ONE-POT SYNTHESIS ;  ONE-STEP CYCLIZATION ;  1,3-DICARBONYL COMPOUNDS ;  SUBSTITUTED DIHYDROFURANS ;  TETRASUBSTITUTED 2,3-DIHYDROFURANS ;  REGIOSELECTIVE SYNTHESIS ;  EFFICIENT SYNTHESIS ;  RADICAL SYNTHESIS ;  TANDEM REACTION ;  IONIC LIQUIDS
语种: 英语
WOS记录号: WOS:000342761700043
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/145866
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China

Recommended Citation:
Zhu, Fu-Lin,Wang, Ya-Hui,Zhang, De-Yang,et al. Enantioselective Synthesis of Highly Functionalized Dihydrofurans through Copper-Catalyzed Asymmetric Formal [3+2] Cycloaddition of beta-Ketoesters with Propargylic Esters[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2014,53(38):10223-10227.
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