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Enantioselective synthesis of quaternary alpha-aminophosphonates by organocatalytic Friedel-Crafts reactions of indoles with cyclic alpha-ketiminophosphonates
Yan, Zhong; Gao, Xiang; Zhou, Yong-Gui
KeywordFriedel-crafts Reaction Quaternary Alpha-aminophosphonate Indole Chiral Phosphoric Acid
Source PublicationCHINESE JOURNAL OF CATALYSIS
2017-05-01
DOI10.1016/S1872-2067(17)62804-3
Volume38Pages:784-792
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences ; Technology
WOS SubjectChemistry, Applied ; Chemistry, Physical ; Engineering, Chemical
WOS Research AreaChemistry ; Engineering
WOS KeywordCHIRAL PHOSPHORIC-ACID ; C BOND FORMATION ; ASYMMETRIC-SYNTHESIS ; BRONSTED ACID ; STEREOSELECTIVE-SYNTHESIS ; ALKYLATION REACTION ; DERIVATIVES ; AMINO ; CONSTRUCTION ; IMINES
AbstractAn efficient asymmetric Friedel-Crafts reaction has been developed for the synthesis of optically active quaternary alpha-aminophosphonates with up to 98% ee. The synthesis involves the reaction of cyclic alpha-ketiminophosphonates with indoles using an H8-BINOL-derived chiral phosphoric acid (CPA) catalyst that bears electron-withdrawing 3,5-ditrifluoromethylphenyl substituents on its 3- and 3'-positions. This Friedel-Crafts reaction of cyclic alpha-ketiminophosphonates was also successful with pyrrole. (C) 2017, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.
Language英语
WOS IDWOS:000402346400003
Citation statistics
Cited Times:4[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/152281
Collection中国科学院大连化学物理研究所
AffiliationChinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Liaoning, Peoples R China
Recommended Citation
GB/T 7714
Yan, Zhong,Gao, Xiang,Zhou, Yong-Gui. Enantioselective synthesis of quaternary alpha-aminophosphonates by organocatalytic Friedel-Crafts reactions of indoles with cyclic alpha-ketiminophosphonates[J]. CHINESE JOURNAL OF CATALYSIS,2017,38:784-792.
APA Yan, Zhong,Gao, Xiang,&Zhou, Yong-Gui.(2017).Enantioselective synthesis of quaternary alpha-aminophosphonates by organocatalytic Friedel-Crafts reactions of indoles with cyclic alpha-ketiminophosphonates.CHINESE JOURNAL OF CATALYSIS,38,784-792.
MLA Yan, Zhong,et al."Enantioselective synthesis of quaternary alpha-aminophosphonates by organocatalytic Friedel-Crafts reactions of indoles with cyclic alpha-ketiminophosphonates".CHINESE JOURNAL OF CATALYSIS 38(2017):784-792.
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