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N-Heterocyclic Carbene Catalyzed Enantioselective [3+2] Dearomatizing Annulation of Saturated Carboxylic Esters with N-Iminoisoquinolinium Ylides

文献类型：期刊论文

作者Zhang, Pengfei1,2,5; Zhou, Yu3,4,5; Han, Xu3,4,5; Xu, Jinyi1,2; Liu, Hong3,4,5
刊名JOURNAL OF ORGANIC CHEMISTRY
出版日期2018-04-06
卷号83期号:7页码:3879-3888
ISSN号0022-3263
DOI10.1021/acs.joc.8b00227
文献子类Article
英文摘要The dearomatizing annulation reaction is a significant challenge in organic chemistry. The direct activation of a carbons of simple saturated esters, as nucleophiles, is an important synthesis strategy. In the present study, we disclose [3 + 2] dearomatizing annulation reactions with direct activating alpha-carbons of saturated carboxylic esters and N-iminoisoquinolinium ylides, which possess highly enantioselective characteristics, catalyzed by N-heterocyclic carbenes (NHCs). The protocol achieves isoquinoline dearomatization and the construction of tricyclic chiral products under mild conditions with good yield, substrate tolerance, and diastereoselectivity as well as excellent enantioselectivity.
WOS关键词GAMMA-CARBON ACTIVATION ; AZOMETHINE IMINES ; ORGANOCATALYTIC ACTIVATION ; ALPHA-CHLOROALDEHYDES ; ACCESS ; CYCLOADDITION ; ALDEHYDES ; ENALS ; SPIROCYCLIZATION ; INDOLIZIDINE
资助项目National Natural Science Foundation of China[21672232] ; National Natural Science Foundation of China[81673306] ; National Natural Science Foundation of China[81703348]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:000429886100044
出版者AMER CHEMICAL SOC
源URL[http://119.78.100.183/handle/2S10ELR8/279809]  
专题药物化学研究室
中科院受体结构与功能重点实验室
新药研究国家重点实验室
通讯作者Xu, Jinyi; Liu, Hong
作者单位1.China Pharmaceut Univ, Dept Med Chem, 24 Tong Jia Xiang, Nanjing 210009, Jiangsu, Peoples R China;
2.China Pharmaceut Univ, State Key Lab Nat Med, 24 Tong Jia Xiang, Nanjing 210009, Jiangsu, Peoples R China;
3.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China
4.Chinese Acad Sci, Shanghai Inst Mat Med, Key Lab Receptor Res, 555 Zu Chong Zhi Rd, Shanghai 201203, Peoples R China;
5.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zu Chong Zhi Rd, Shanghai 201203, Peoples R China;
推荐引用方式
GB/T 7714		 Zhang, Pengfei,Zhou, Yu,Han, Xu,et al. N-Heterocyclic Carbene Catalyzed Enantioselective [3+2] Dearomatizing Annulation of Saturated Carboxylic Esters with N-Iminoisoquinolinium Ylides[J]. JOURNAL OF ORGANIC CHEMISTRY,2018,83(7):3879-3888.
APA Zhang, Pengfei,Zhou, Yu,Han, Xu,Xu, Jinyi,&Liu, Hong.(2018).N-Heterocyclic Carbene Catalyzed Enantioselective [3+2] Dearomatizing Annulation of Saturated Carboxylic Esters with N-Iminoisoquinolinium Ylides.JOURNAL OF ORGANIC CHEMISTRY,83(7),3879-3888.
MLA Zhang, Pengfei,et al."N-Heterocyclic Carbene Catalyzed Enantioselective [3+2] Dearomatizing Annulation of Saturated Carboxylic Esters with N-Iminoisoquinolinium Ylides".JOURNAL OF ORGANIC CHEMISTRY 83.7(2018):3879-3888.

入库方式： OAI收割

来源：上海药物研究所

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