Transition Metal-Catalyzed Asymmetric Addition of Organoboron Reagents to Aldehydes and Ketones
文献类型：期刊论文
| 作者 | Zhu Dong-Xing1; Xu Ming-Hua1,2,3
|
| 刊名 | CHINESE JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2020-02-25 |
| 卷号 | 40期号:2页码:255-275 |
| 关键词 | asymmetric synthesis chiral alcohols organoboron reagents transition-metal catalysis asymmetric addition |
| ISSN号 | 0253-2786 |
| DOI | 10.6023/cjoc201910009 |
| 通讯作者 | Xu Ming-Hua(xumh@sustech.edu.cn) |
| 英文摘要 | Chiral aryl alcohols are prevalent in a broad range of biologically active compounds, pharmaceutical agents and natural products. They also constitute a broad class of optically active building blocks for the synthesis of important chiral compounds. In recent years, organoboron reagents are widely used in organic synthesis as they possess advantages of ready availability, low toxicity, good air and moisture stability as well as high functional group compatibility. Since the first report of rhodium-catalyzed asymmetric addition of aryl boronic acids to aryl aldehydes in 1998 by Miyaura, the use of organoboron reagents in asymmetric addition to various carbonyl compounds under various transition-metal catalyses has been intensively investigated. Over the past two decades, transition metal-catalyzed asymmetric addition of organoboron reagents to aldehydes and ketones has proved as one of the most direct and powerful methods for accessing versatile optically active alcohols. The development and progress of a wide range of chiral ligands for Rh, Ru, Pd, Ir, Cu, Ni and Co catalysis for asymmetric addition of organoboron reagents to aldehydes and ketones are summarized, and the achievements in enantioselective synthesis of chiral aryl alcohols and their applications in the synthesis of related biocative products are described. Among them, rhodium and ruthenium-catalyzed enantioselective additions have received considerable attention. In the cases of activated carbonyl compounds such as alpha-aryl ketoesters and alpha-diaryl diketones, excellent results can be attained in terms of both yield and enantioselectivity. However, it remains a daunting challenge for highly enantioselective addition to simple unactivated aldehydes and ketones owing to the difficulty in overcoming stereo differentiation. Future efforts in the community would focus on developing new effective transition-metal catalysts in addressing these issues by promoting efficient transformation and controlling excellent enantioselectivity. |
| WOS关键词 | HIGHLY ENANTIOSELECTIVE SYNTHESIS ; ARYLBORONIC ACIDS ; ALPHA-KETOESTERS ; OLEFIN LIGANDS ; INTRAMOLECULAR ADDITION ; RECEPTOR LIGANDS ; ME-BIPAM ; ARYLATION ; 1,2-ADDITION ; COMPLEXES |
| 资助项目 | National Natural Science Foundation of China[21672229] ; National Natural Science Foundation of China[81521005] ; National Natural Science Foundation of China[21971103] ; National Science & Technology Major Project of China[2018ZX09711002-006] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000522786900001 |
| 出版者 | SCIENCE PRESS |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/280925]  |
| 专题 | 新药研究国家重点实验室 |
| 通讯作者 | Xu Ming-Hua |
| 作者单位 | 1.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China 2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Guangdong, Peoples R China 3.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China |
| 推荐引用方式 GB/T 7714 | Zhu Dong-Xing,Xu Ming-Hua. Transition Metal-Catalyzed Asymmetric Addition of Organoboron Reagents to Aldehydes and Ketones[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY,2020,40(2):255-275. |
| APA | Zhu Dong-Xing,&Xu Ming-Hua.(2020).Transition Metal-Catalyzed Asymmetric Addition of Organoboron Reagents to Aldehydes and Ketones.CHINESE JOURNAL OF ORGANIC CHEMISTRY,40(2),255-275. |
| MLA | Zhu Dong-Xing,et al."Transition Metal-Catalyzed Asymmetric Addition of Organoboron Reagents to Aldehydes and Ketones".CHINESE JOURNAL OF ORGANIC CHEMISTRY 40.2(2020):255-275. |
入库方式： OAI收割
来源：上海药物研究所
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