Enantioconvergent Copper Catalysis: In Situ Generation of the Chiral Phosphorus Ylide and Its Wittig Reactions | |
Department | OSSO国家重点实验室 |
Zhang, Kai1; Lu, Liang-Qiu1,2; Yao, Sheng1; Chen, Jia-Rong1; Shi, De-Qing1; Xiao, Wen-Jing1,3 | |
2017 | |
Source Publication | Journal of the American Chemical Society |
ISSN | 0002-7863 |
Volume | 139Issue:36Pages:12847-12854 |
Abstract | The Wittig reaction, which produces alkenes from phosphorus ylides (P-ylides) and carbonyls, is one of the most powerful tools in chemical synthesis. This Nobel Prize-winning reaction is widely used in natural product synthesis, fine chemical production (i.e., medicines and agricultural agents), and polymer functionalization. Despite these great achievements, the potential of the Wittig reaction, particularly regarding the access of chiral alkene building blocks, has not been fully exploited. The main area that requires additional exploration is the development of general and practical methods to efficiently prepare chiral P-ylides. Here, we show that highly functionalized chiral P-ylides can be easily synthesized through a copper-catalyzed asymmetric propargylic alkylation reaction from phosphonium salts and racemic propargylic esters. The subsequent Wittig reactions enable the synthesis of versatile alkene building blocks, chiral α-propargylic acrylates, and α-propargylic allenoates, with a wide substrate scope and satisfactory functional group compatibility. This transformation features inexpensive transition-metal catalysts, user-friendly conditions, easily available feedstock, and high-valued products. |
Subject Area | 物理化学与绿色催化 |
DOI | 10.1021/jacs.7b08207 |
Funding Organization | the National Natural Science Foundation of China (nos. 21472057;21472058;21572074;21622201;21772052);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);Outstanding Youth Foundation of Hubei Province (2015CFA033) |
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/362003/22506 |
Collection | 羰基合成与选择氧化国家重点实验室(OSSO) |
Corresponding Author | Xiao, Wen-Jing |
Affiliation | 1.Cent China Normal Univ, Hubei Int Sci & Technol Cooperat Base Pesticide &, Key Lab Pesticide & Chem Biol, Minist Educ,Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China 2.Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China 3.Tianjin Univ, Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300072, Peoples R China |
Recommended Citation GB/T 7714 | Zhang, Kai,Lu, Liang-Qiu,Yao, Sheng,et al. Enantioconvergent Copper Catalysis: In Situ Generation of the Chiral Phosphorus Ylide and Its Wittig Reactions[J]. Journal of the American Chemical Society,2017,139(36):12847-12854. |
APA | Zhang, Kai,Lu, Liang-Qiu,Yao, Sheng,Chen, Jia-Rong,Shi, De-Qing,&Xiao, Wen-Jing.(2017).Enantioconvergent Copper Catalysis: In Situ Generation of the Chiral Phosphorus Ylide and Its Wittig Reactions.Journal of the American Chemical Society,139(36),12847-12854. |
MLA | Zhang, Kai,et al."Enantioconvergent Copper Catalysis: In Situ Generation of the Chiral Phosphorus Ylide and Its Wittig Reactions".Journal of the American Chemical Society 139.36(2017):12847-12854. |
Files in This Item: | ||||||
File Name/Size | DocType | Version | Access | License | ||
jacs.7b08207.pdf(1797KB) | 期刊论文 | 作者接受稿 | 开放获取 | CC BY-NC-SA | View Application Full Text |
Items in the repository are protected by copyright, with all rights reserved, unless otherwise indicated.
Edit Comment