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

页码：8302 / 8307

页数：6

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