Desilylation-Activated Propargylic Transformation: Enantioselective Copper-Catalyzed [3+2] Cycloaddition of Propargylic Esters with -Naphthol or Phenol Derivatives

doi:10.1002/anie.201510793

	Desilylation-Activated Propargylic Transformation: Enantioselective Copper-Catalyzed [3+2] Cycloaddition of Propargylic Esters with -Naphthol or Phenol Derivatives
	Xu, Jie 1; Shao, Long 1,2; Wang, Ya-Hui 1; Zhang, De-Yang 1,2; Hu, Xiang-Ping 1
刊名	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
	2016-04-11
卷号	55 期号:16 页码:5014-5018
关键词	Asymmetric Catalysis Cycloaddition Copper Heterocycles Reaction Mechanisms
ISSN号	1433-7851
DOI	10.1002/anie.201510793
文献子类	Article
英文摘要	A copper-catalyzed asymmetric [3+2] cycloaddition of 3-trimethylsilylpropargylic esters with either -naphthols or electron-rich phenols has been realized and proceeds by a desilylation-activated process. Under the catalysis of Cu(OAc)(2)H2O in combination with a structurally optimized ketimine P,N,N-ligand, a wide range of optically active 1,2-dihydronaphtho[2,1-b]furans or 2,3-dihydrobenzofurans were obtained in good yields and with high enantioselectivities (up to 96% ee). This represents the first desilylation-activated catalytic asymmetric propargylic transformation.
WOS关键词	ALKYNYL GROUP-TRANSFER ; SUBSTITUTION-REACTIONS ; COUPLING REACTIONS ; BETA-KETOESTERS ; ALCOHOLS ; AMINATION ; ALKYLATION ; ACETATES ; AMINES ; CU
WOS研究方向	Chemistry
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000374496100025
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/170762]
专题	大连化学物理研究所_中国科学院大连化学物理研究所
通讯作者	Hu, Xiang-Ping
作者单位	1.Chinese Acad Sci, Dalian Inst Chem Phys, 457 Zhongshan Rd, Dalian 116023, Peoples R China 2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
推荐引用方式 GB/T 7714	Xu, Jie,Shao, Long,Wang, Ya-Hui,et al. Desilylation-Activated Propargylic Transformation: Enantioselective Copper-Catalyzed [3+2] Cycloaddition of Propargylic Esters with -Naphthol or Phenol Derivatives[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2016,55(16):5014-5018.
APA	Xu, Jie,Shao, Long,Wang, Ya-Hui,Zhang, De-Yang,&Hu, Xiang-Ping.(2016).Desilylation-Activated Propargylic Transformation: Enantioselective Copper-Catalyzed [3+2] Cycloaddition of Propargylic Esters with -Naphthol or Phenol Derivatives.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,55(16),5014-5018.
MLA	Xu, Jie,et al."Desilylation-Activated Propargylic Transformation: Enantioselective Copper-Catalyzed [3+2] Cycloaddition of Propargylic Esters with -Naphthol or Phenol Derivatives".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 55.16(2016):5014-5018.