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Photoinduced carbene transfer for copper-catalyzed asymmetric [4 + 1] cycloadditions: an entry to chiral indolines bearing quaternary stereocenters

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成果类型:
期刊论文
作者:
Qu, Bao-Le;Shi, Bin;He, Lin;Shi, Jun-Wei;Xiao, Wen-Jing;...
通讯作者:
Lu, LQ
作者机构:
[Lu, Liang-Qiu; Lu, LQ; He, Lin; Qu, Bao-Le; Xiao, Wen-Jing; Shi, Jun-Wei; Shi, Bin] Cent China Normal Univ, Coll Chem, CCNU uOttawa Joint Res Ctr, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.
[Lu, Liang-Qiu] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China.
[Lu, Liang-Qiu] Chinese Acad Sci, Lanzhou Inst Chem Phys LICP, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China.
通讯机构:
[Lu, LQ ] C
Cent China Normal Univ, Coll Chem, CCNU uOttawa Joint Res Ctr, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.
语种:
英文
关键词:
Copper;Cycloaddition;Organic compounds;Stereochemistry;Carbene transfer;Copper catalyzed;Cycloadditions;Diastereoselectivities;Enantio;Hotspots;Photo-induced;Quaternary stereocenters;Sulfur ylides;Synthetic chemistry;Catalysis
期刊:
Organic Chemistry Frontiers
ISSN:
2052-4110
年:
2023
卷:
10
期:
14
页码:
3498-3503
基金类别:
This work was financially supported by the National Key Research and Development Program of China (2018YFA0209401), the National Natural Science Foundation of China (22171053), and the Natural Science Foundation of Shanghai (21ZR1409600). We are grateful to the National Natural Science Foundation of China (no. 22271113, 92256301, 21820102003 and 91956201) 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:
Indoline skeletons are widely found in many natural isolates and pharmaceuticals, making indoline synthesis an ongoing research hotspot in synthetic chemistry. However, the catalytic asymmetric de novo construction of indolines bearing chiral quaternary stereocenters remains challenging. Herein, we present a solution to this unmet challenge through copper-catalyzed asymmetric [4 + 1] cycloadditions of ethynylbenzoxazinones with sulfur ylides, which are formed in situ by photoinduced carbene transfer. As a result, a wide range of chiral indoline...

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