Asymmetric Formal Vinylogous Iminium Ion Activation for Vinyl-Substituted Heteroaryl and Aryl Aldehydes

被引：31
作者：
Gao, Xin-Yue [1 ,2 ]
Yan, Ru-Jie [1 ,2 ]
Xiao, Ben-Xian [1 ,2 ]
Du, Wei [1 ,2 ]
Albrecht, Lukasz [3 ]
Chen, Ying-Chun [1 ,2 ]
机构：
[1] Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Minist Educ, West China Sch Pharm, Chengdu 610041, Peoples R China
[2] Sichuan Univ, West China Sch Pharm, Sichuan Res Ctr Drug Precis Ind Technol, Chengdu 610041, Peoples R China
[3] Lodz Univ Technol, Dept Chem, Inst Organ Chem, Zeromskiego 116, PL-90924 Lodz, Poland
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 23期
关键词：
DIELS-ALDER REACTION; 3+2 CYCLOADDITION; N-2,2,2-TRIFLUOROETHYLISATIN KETIMINES; 1,3-DIPOLAR CYCLOADDITION; 3-FURFURAL DERIVATIVES; MICHAEL ADDITION; TRIENAMINE; SPIROOXINDOLES; NITRONES; CONSTRUCTION;
D O I：
10.1021/acs.orglett.9b03794
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The vinyl group tethered to furfurals could be LUMO-lowered by forming formal vinylogous iminium ion intermediates catalyzed by a chiral secondary amine and underwent asymmetric [3 + 2] cycloaddition reactions with N-trifluoroethyl-substituted isatin imines, furnishing a variety of spirooxindoles incorporating a 3,2'-pyrrolidine motif with excellent stereo selectivity. In addition, this strategy has been successfully expanded to a number of vinyl-substituted electron-rich heteroaryl aldehydes and even some specific aryl aldehydes.
引用
收藏
页码：9628 / 9632
页数：5
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