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Copper-Catalyzed Asymmetric Formal [3+2] Cycloaddition of Propargylic Acetates with Hydrazines: Enantioselective Synthesis of Optically Active 2-Pyrazolines
Zhang, De-Yang1,2; Shao, Long1,2; Xu, Jie1; Hu, Xiang-Ping1
KeywordAsymmetric Catalysis Copper Cycloaddition Propargylic Ester 2-pyrazoline
Source PublicationACS CATALYSIS
2015-09-01
DOI10.1021/acscatal.5b01283
Volume5Issue:9Pages:5026-5030
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Physical
WOS Research AreaChemistry
WOS KeywordAZOMETHINE IMINES ; 1,3-DIPOLAR CYCLOADDITION ; NITRILE IMINES ; SUBSTITUTION-REACTIONS ; 1,3-DICARBONYL COMPOUNDS ; BETA-KETOESTERS ; LEWIS-ACID ; AMINATION ; ESTERS ; DERIVATIVES
AbstractA catalytic asymmetric [3 + 2] cycloaddition of hydrazines to bis-electrophilic C3 synthons generated from propargylic acetates, followed by an intramolecular 1,3-H migration, for the regio- and enantioselective construction of chiral 2-pyrazolines has been reported. By employment of copper catalysis in combination with a structurally rigid tridentate P,N,N-ligand, a variety of chiral 2-pyrazolines were obtained in good yields and with high enantioselectivities (up to 96% ee). A possible transition state has been proposed to explain the origin of the regio- and enantioselectivities.
Language英语
WOS IDWOS:000361089700008
Citation statistics
Cited Times:36[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/146529
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
Zhang, De-Yang,Shao, Long,Xu, Jie,et al. Copper-Catalyzed Asymmetric Formal [3+2] Cycloaddition of Propargylic Acetates with Hydrazines: Enantioselective Synthesis of Optically Active 2-Pyrazolines[J]. ACS CATALYSIS,2015,5(9):5026-5030.
APA Zhang, De-Yang,Shao, Long,Xu, Jie,&Hu, Xiang-Ping.(2015).Copper-Catalyzed Asymmetric Formal [3+2] Cycloaddition of Propargylic Acetates with Hydrazines: Enantioselective Synthesis of Optically Active 2-Pyrazolines.ACS CATALYSIS,5(9),5026-5030.
MLA Zhang, De-Yang,et al."Copper-Catalyzed Asymmetric Formal [3+2] Cycloaddition of Propargylic Acetates with Hydrazines: Enantioselective Synthesis of Optically Active 2-Pyrazolines".ACS CATALYSIS 5.9(2015):5026-5030.
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