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Enantioselective Synthesis of Highly Functionalized Dihydrofurans through Copper-Catalyzed Asymmetric Formal [3+2] Cycloaddition of beta-Ketoesters with Propargylic Esters
Zhu, Fu-Lin1,2; Wang, Ya-Hui1; Zhang, De-Yang1,2; Xu, Jie1; Hu, Xiang-Ping1
KeywordAsymmetric Catalysis 2 Copper 3-dihydrofurans Cycloadditions Synthetic Methods
Source PublicationANGEWANDTE CHEMIE-INTERNATIONAL EDITION
2014-09-15
DOI10.1002/anie.201405857
Volume53Issue:38Pages:10223-10227
Indexed BySCI ; IC ; CCR
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Multidisciplinary
WOS Research AreaChemistry
WOS KeywordONE-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
AbstractAn 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.
Language英语
WOS IDWOS:000342761700043
Citation statistics
Cited Times:72[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/145866
Collection中国科学院大连化学物理研究所
Affiliation1.Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
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.
APA Zhu, Fu-Lin,Wang, Ya-Hui,Zhang, De-Yang,Xu, Jie,&Hu, Xiang-Ping.(2014).Enantioselective Synthesis of Highly Functionalized Dihydrofurans through Copper-Catalyzed Asymmetric Formal [3+2] Cycloaddition of beta-Ketoesters with Propargylic Esters.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,53(38),10223-10227.
MLA Zhu, Fu-Lin,et al."Enantioselective Synthesis of Highly Functionalized Dihydrofurans through Copper-Catalyzed Asymmetric Formal [3+2] Cycloaddition of beta-Ketoesters with Propargylic Esters".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 53.38(2014):10223-10227.
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