Diastereo- and Enantioselective Copper-Catalyzed Decarboxylative Ring-Opening [3+2] Annulation of Tertiary Propargylic Carbamates through Regioselective alpha-Attack of gamma-Butenolides

doi:10.1021/acs.orglett.9b03081

	Diastereo- and Enantioselective Copper-Catalyzed Decarboxylative Ring-Opening [3+2] Annulation of Tertiary Propargylic Carbamates through Regioselective alpha-Attack of gamma-Butenolides
	Xu, You-Wei 1,2; Hu, Xiang-Ping 1
刊名	ORGANIC LETTERS
	2019-10-04
卷号	21 期号:19 页码:8091-8096
ISSN号	1523-7060
DOI	10.1021/acs.orglett.9b03081
通讯作者	Hu, Xiang-Ping(xiangping@dicp.ac.cn)
英文摘要	A copper-catalyzed regio-, diastereo-, and enantioselective decarboxylative ring-opening [3 + 2] annulation of tertiary propargylic carbamates with gamma-butenolides for the synthesis of optically active pyrrolidinones has been realized. The reaction proceeded through regioselective alpha-attack of gamma-butenolide and generated highly congested vicinal tertiary and all-carbon quaternary stereocenters in pyrrolidinone scaffolds, featuring high stereoselective induction and broad functional group tolerance. Critical to the successful development of this method was the employment of copper catalysis in concert with a diPh-Pybox ligand.
资助项目	National Natural Science Foundation of China[21572226] ; National Natural Science Foundation of China[21772196] ; Dalian Science and Technology Innovation Project[2018J12GX054]
WOS关键词	ALLYLIC ALKYLATION ; CONSTRUCTION ; ESTERS ; CYCLOADDITION ; ACETATES ; PYBOX
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000489200100083
资助机构	National Natural Science Foundation of China ; National Natural Science Foundation of China ; Dalian Science and Technology Innovation Project ; Dalian Science and Technology Innovation Project ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Dalian Science and Technology Innovation Project ; Dalian Science and Technology Innovation Project ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Dalian Science and Technology Innovation Project ; Dalian Science and Technology Innovation Project ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Dalian Science and Technology Innovation Project ; Dalian Science and Technology Innovation Project
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/172541]
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, 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, You-Wei,Hu, Xiang-Ping. Diastereo- and Enantioselective Copper-Catalyzed Decarboxylative Ring-Opening [3+2] Annulation of Tertiary Propargylic Carbamates through Regioselective alpha-Attack of gamma-Butenolides[J]. ORGANIC LETTERS,2019,21(19):8091-8096.
APA	Xu, You-Wei,&Hu, Xiang-Ping.(2019).Diastereo- and Enantioselective Copper-Catalyzed Decarboxylative Ring-Opening [3+2] Annulation of Tertiary Propargylic Carbamates through Regioselective alpha-Attack of gamma-Butenolides.ORGANIC LETTERS,21(19),8091-8096.
MLA	Xu, You-Wei,et al."Diastereo- and Enantioselective Copper-Catalyzed Decarboxylative Ring-Opening [3+2] Annulation of Tertiary Propargylic Carbamates through Regioselective alpha-Attack of gamma-Butenolides".ORGANIC LETTERS 21.19(2019):8091-8096.