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Pd-Catalyzed Asymmetric Acyl-Carbamoylation of an Alkene to Construct an alpha-Quaternary Chiral Cycloketone

文献类型：期刊论文

作者Liu, Min1,2; Wang, Xing1,2; Guo, Ziqiong1; Li, Hanyuan1; Huang, Wei3; Xu, Hui1,2; Dai, Hui-Xiong1,2
刊名ORGANIC LETTERS
出版日期2021-08-20
卷号23期号:16页码:6299-6304
ISSN号1523-7060
DOI10.1021/acs.orglett.1c02093
通讯作者Xu, Hui(xuhui2018@simm.ac.cn) ; Dai, Hui-Xiong(hxdai@simm.ac.cn)
英文摘要Herein, we report the palladium-catalyzed asymmetric acyl-carbamoylation of an alkene by employing thioesters as the acyl electrophiles and t-BuNC as the carbamoyl reagent, affording an alpha-quaternary chiral cycloketone in synthetically useful yields with excellent enantioselectivity. The reaction proceeded via asymmetric 1,2-migratory insertions of acyl-Pd into alkenes and subsequent migratory insertion of isocyanides into C(sp(3))-Pd-II. The product could be diversified to some valuable skeletons with retention of enantiopurity, demonstrating the synthetic utility of this protocol.
WOS关键词C BOND FORMATION ; ENANTIOSELECTIVE CONSTRUCTION ; HECK REACTION ; THIOL ESTERS ; PALLADIUM ; THIOESTERS ; STEREOCENTERS ; CYCLIZATION ; CLEAVAGE ; CARBOACYLATION
资助项目Shanghai Institute of Materia Medica ; Chinese Academy of Sciences ; National Natural Science Foundation of China[21772211] ; National Natural Science Foundation of China[21920102003] ; Youth Innovation Promotion Association CAS[2014229] ; Youth Innovation Promotion Association CAS[2018293] ; Institutes for Drug Discovery and Development, Chinese Academy of Sciences[CASIMM0120163006] ; Science and Technology Commission of Shanghai Municipality[17JC1405000] ; Science and Technology Commission of Shanghai Municipality[21ZR1475400] ; Science and Technology Commission of Shanghai Municipality[18431907100] ; Program of Shanghai Academic Research Leader[19XD1424600] ; National Science & Technology Major Project Key New Drug Creation and Manufacturing Program, China[2018ZX09711002-006]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:000687930500023
出版者AMER CHEMICAL SOC
源URL[http://119.78.100.183/handle/2S10ELR8/297790]  
专题中国科学院上海药物研究所
通讯作者Xu, Hui; Dai, Hui-Xiong
作者单位1.Chinese Acad Sci, Key Lab Receptor Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
3.Nanchang Univ, Sch Pharm, Nanchang 330006, Jiangxi, Peoples R China
推荐引用方式
GB/T 7714		 Liu, Min,Wang, Xing,Guo, Ziqiong,et al. Pd-Catalyzed Asymmetric Acyl-Carbamoylation of an Alkene to Construct an alpha-Quaternary Chiral Cycloketone[J]. ORGANIC LETTERS,2021,23(16):6299-6304.
APA Liu, Min.,Wang, Xing.,Guo, Ziqiong.,Li, Hanyuan.,Huang, Wei.,...&Dai, Hui-Xiong.(2021).Pd-Catalyzed Asymmetric Acyl-Carbamoylation of an Alkene to Construct an alpha-Quaternary Chiral Cycloketone.ORGANIC LETTERS,23(16),6299-6304.
MLA Liu, Min,et al."Pd-Catalyzed Asymmetric Acyl-Carbamoylation of an Alkene to Construct an alpha-Quaternary Chiral Cycloketone".ORGANIC LETTERS 23.16(2021):6299-6304.

入库方式： OAI收割

来源：上海药物研究所

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