Enantioselective Construction of C4-Quaternary Quinolinones via Copper(II)-Catalyzed Asymmetric [1,3] O-to-C Rearrangement

被引：3
|
作者：
Xiong, Zongli [1 ,2 ]
Xu, Fuxing [1 ,2 ]
Zhou, Yuqiao [3 ]
Zhang, Rong [1 ,2 ]
Zhang, Yulong [4 ]
Chen, Yushuang [6 ]
Yao, Weijun [5 ]
Wang, Zhen [1 ,2 ]
机构：
[1] Chongqing Univ, Sch Pharmaceut Sci, Chongqing 401331, Peoples R China
[2] Chongqing Univ, Chongqing Key Lab Nat Drug Res, Chongqing 401331, Peoples R China
[3] Sichuan Univ, Coll Chem, Key Lab Green Chem & Technol, Minist Educ, Chengdu 610064, Peoples R China
[4] Chongqing Normal Univ, Chongqing Key Lab Green Synth & Applicat, Chongqing 401331, Peoples R China
[5] Zhejiang Sci Tech Univ, Dept Chem, Hangzhou 310000, Zhejiang, Peoples R China
[6] Chongqing Univ Sci & Technol, Coll Chem & Chem Engn, Chongqing 401331, Peoples R China
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 46期
关键词：
DIELS-ALDER REACTIONS; NITROGEN-HETEROCYCLES; RING-EXPANSION; ISATINS; TRIFLUOROMETHYLATION; FLUORINATION; CATALYSIS;
D O I：
10.1021/acs.orglett.3c03378
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient asymmetric [1,3] O-to-C rearrangement of quinolin-2(1H)-ones enabled by a chiral bisoxazoline/copper complex has been developed. This strategy tolerated a wide range of substrates to provide a series of 1,4-dihydroquinoline-2,3-diones containing a quaternary stereocenter. A further cyclization of the [1,3] O-to-C rearrangement products was also realized, which led to various optically active 3,4-dihydroquinolin-2-ones with broad substrate scope.
引用
收藏
页码：8302 / 8307
页数：6
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