Rhodium(I)-Catalyzed Enantioselective C(sp(3))-H Functionalization via Carbene-Induced Asymmetric Intermolecular C-H Insertion(dagger)
文献类型：期刊论文
| 作者 | Liu, Bo1,2,3; Xu, Ming-Hua1,2 |
| 刊名 | CHINESE JOURNAL OF CHEMISTRY
 |
| 出版日期 | 2021-05-27 |
| 页码 | 5 |
| 关键词 | Asymmetric catalysis C-H functionalization carbene C-H insertion Rhodium |
| ISSN号 | 1001-604X |
| DOI | 10.1002/cjoc.202100040 |
| 通讯作者 | Xu, Ming-Hua(xumh@sustech.edu.cn) |
| 英文摘要 | Main observation and conclusion Transition-metal-catalyzed C-H insertion of metal-carbene represents an excellent and powerful approach for C-H functionalization. However, despite remarkable advances in metal-carbene chemistry, transition metal catalysts that are capable of enantioselective intermolecular carbene C-H insertion are mainly constrained to dirhodium(II) and iridium(III)-based complexes. Herein, we disclose a new version of asymmetric carbene C-H insertion reaction with rhodium(I) catalyst. A highly enantioselective rhodium(I) complex-catalyzed C(sp(3))-H functionalization of 1,4-cyclohexadienes with alpha-aryl-alpha-diazoacetates was successfully developed. By using chiral bicyclo[2.2.2]-octadiene as ligand, rhodium(I)-carbene-induced asymmetric intermolecular C-H insertion proceeds smoothly at room temperature, allowing access to a diverse variety of alpha-aryl-alpha-cyclohexadienyl acetates and gem-diaryl-containing acetates in good yields with good to excellent enantioselectivities (up to 99% ee). Furthermore, the synthetic utility of the reaction was highlighted by facile synthesis of a novel cannabinoid CB1 receptor ligand. This method may offer a new opportunity for the development of therapeutically exploitable cannabinoid receptor type ligands in medicinal chemistry. |
| WOS关键词 | ARYL-ALPHA-DIAZOACETATES ; BOND FUNCTIONALIZATION ; STEREOSELECTIVE FUNCTIONALIZATION ; CANNABINOID CB1 ; SULFUR-OLEFINS ; CHIRAL LIGANDS ; ARYLATION ; CONSTRUCTION ; PHENOLS ; ACCESS |
| 资助项目 | National Natural Science Foundation of China[21971103] ; National Natural Science Foundation of China[21672229] ; National Science & Technology Major Project Key New Drug Creation and Manufacturing Program, China[2018ZX09711002-006] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002] ; Guangdong Provincial Key Laboratory of Catalysis[(1R,4R)-5] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000655102200001 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/297224]  |
| 专题 | 中国科学院上海药物研究所 |
| 通讯作者 | Xu, Ming-Hua |
| 作者单位 | 1.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, 1088 Xueyuan Blvd, Shenzhen 518055, Guangdong, Peoples R China 2.Southern Univ Sci & Technol, Dept Chem, Guangdong Prov Key Lab Catalysis, 1088 Xueyuan Blvd, Shenzhen 518055, Guangdong, Peoples R China 3.Chinese Acad Sci, Shanghai Inst Mat Med, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Liu, Bo,Xu, Ming-Hua. Rhodium(I)-Catalyzed Enantioselective C(sp(3))-H Functionalization via Carbene-Induced Asymmetric Intermolecular C-H Insertion(dagger)[J]. CHINESE JOURNAL OF CHEMISTRY,2021:5. |
| APA | Liu, Bo,&Xu, Ming-Hua.(2021).Rhodium(I)-Catalyzed Enantioselective C(sp(3))-H Functionalization via Carbene-Induced Asymmetric Intermolecular C-H Insertion(dagger).CHINESE JOURNAL OF CHEMISTRY,5. |
| MLA | Liu, Bo,et al."Rhodium(I)-Catalyzed Enantioselective C(sp(3))-H Functionalization via Carbene-Induced Asymmetric Intermolecular C-H Insertion(dagger)".CHINESE JOURNAL OF CHEMISTRY (2021):5. |
入库方式： OAI收割
来源：上海药物研究所
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