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Enantioselective Trapping of Pd-Containing 1,5-Dipoles by Photogenerated Ketenes: Access to 7-Membered Lactones Bearing Chiral Quaternary Stereocenters

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成果类型:
期刊论文
作者:
Wei, Yi;Liu, Song;Li, Miao-Miao;Li, Yi;Lan, Yu*;...
通讯作者:
Lan, Yu;Xiao, Wen-Jing
作者机构:
[Lu, Liang-Qiu; Xiao, Wen-Jing; Lan, Yu; Xiao, WJ; Li, Miao-Miao; Wei, Yi; Li, Yi] Cent China Normal Univ, Coll Chem, Minist Educ, CCNU uOttawa Joint Res Ctr,Key Lab Pesticide & Ch, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
[Liu, Song; Lan, Yu] Chongqing Univ, Sch Chem & Chem Engn, Chongqing 400030, Peoples R China.
[Xiao, Wen-Jing] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China.
通讯机构:
[Lan, Y; Xiao, WJ; Xiao, Wen-Jing] C
Cent China Normal Univ, Coll Chem, Minist Educ, CCNU uOttawa Joint Res Ctr,Key Lab Pesticide & Ch, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China.
语种:
英文
期刊:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN:
0002-7863
年:
2019
卷:
141
期:
1
页码:
133-137
基金类别:
We are grateful to the National Science Foundation of China (No. 21822103, 21820102003, 21772052, 21772053, 21572074 and 21472057), the Program of Introducing Talents of Discipline to Universities of China (111 Program, B17019) and the Natural Science Foundation of Hubei Province (2017AHB047) for support of this research.
机构署名:
本校为第一且通讯机构
院系归属:
化学学院
摘要:
An enantioselective [5+2] cycloaddition of vinylethylene carbonates and α-diazoketones was achieved for the first time by merging photoactivation and asymmetric Pd catalysis. The key to the success of this method is the enantioselective trapping of Pd-containing, 1,5-dipolar intermediates by ketenes, a class of reactive C2 synthons, which were generated in an in situ and traceless manner under visible light irradiation. Through this trapping, a variety of 7-membered lactones bearing challenging chiral quaternary stereocenters can be accessed i...

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