Sequential Visible-Light Photoactivation and Palladium Catalysis Enabling Enantioselective [4+2] Cycloadditions | |
Department | OSSO国家重点实验室 |
Li, yiao-Miao1; Wei, Yi1; Liu, Jie1; Chen, Hong-Wei1; Lu, Liang-Qiu1,2; Xiao, Wen-Jing1,3 | |
2017 | |
Source Publication | Journal of the American Chemical Society |
ISSN | 0002-7863 |
Volume | 139Issue:41Pages:14707-14713 |
Abstract | Catalytic asymmetric cycloadditions of reactive ketene intermediates provide new opportunities for the production of chiral heterocyclic molecules. Though known for over 100 years, ketenes still remain underexplored in the field of transition-metal (TM)-catalyzed asymmetric cycloadditions because (1) ketenes, as highly electron-deficient species, are possibly unstable to low-valence TMs (i.e., decarbonylation or aggregation) and (2) the conventional thermal synthesis of ketenes from acyl chlorides and amines may be incompatible with TM catalysis (i.e., reactive acyl chloride and amine hydrochloride byproducts). Herein, we detail the unprecedented asymmetric [4+2] cycloaddition of vinyl benzoxazinanones with a variety of ketene intermediates via sequential visible-light photoactivation and palladium catalysis. It is well demonstrated that the traceless and transient generation of ketenes from α-diazoketones through visible-light-induced Wolff rearrangement is important for the success of present cycloaddition. Furthermore, chiral palladium catalysts with a new, chiral hybrid P, S ligand enable asymmetric cycloaddition with high reaction selectivity and enantiocontrol. |
Subject Area | 物理化学与绿色催化 |
DOI | 10.1021/jacs.7b08310 |
Funding Organization | the National Natural Science Foundation of China (Nos. 21472057;21572074;21772052;21772053);the Program of Introducing Talents of Discipline to Universities of China (111 Program, B17019);the Foundation for the Author of National Excellent Doctoral Dissertation of PR China (No. 201422);the Natural Science Foundation of Hubei Province (2015CFA033;2017AH047) |
Indexed By | SCI |
If | 13.858 |
Language | 英语 |
compositor | 第二作者单位 |
Citation statistics | |
Document Type | 期刊论文 |
Identifier | http://ir.licp.cn/handle/362003/22787 |
Collection | 羰基合成与选择氧化国家重点实验室(OSSO) |
Corresponding Author | Lu, Liang-Qiu |
Affiliation | 1.Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol,Minist Educ, Hubei Int Sci & Technol Cooperat Base Pesticide &, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China 2.Chinese Acad Sci, LICP, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China 3.Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300072, Peoples R China |
Recommended Citation GB/T 7714 | Li, yiao-Miao,Wei, Yi,Liu, Jie,et al. Sequential Visible-Light Photoactivation and Palladium Catalysis Enabling Enantioselective [4+2] Cycloadditions[J]. Journal of the American Chemical Society,2017,139(41):14707-14713. |
APA | Li, yiao-Miao,Wei, Yi,Liu, Jie,Chen, Hong-Wei,Lu, Liang-Qiu,&Xiao, Wen-Jing.(2017).Sequential Visible-Light Photoactivation and Palladium Catalysis Enabling Enantioselective [4+2] Cycloadditions.Journal of the American Chemical Society,139(41),14707-14713. |
MLA | Li, yiao-Miao,et al."Sequential Visible-Light Photoactivation and Palladium Catalysis Enabling Enantioselective [4+2] Cycloadditions".Journal of the American Chemical Society 139.41(2017):14707-14713. |
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201714707-14713.pdf(1873KB) | 期刊论文 | 作者接受稿 | 开放获取 | CC BY-NC-SA | View Application Full Text |
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