Enantioselective Tsuji-Trost α-Fluoroallylation of Amino Acid Esters with Gem-Difluorinated Cyclopropanes
文献类型：期刊论文
| 作者 | Su, Zheng4; Tan, Binhong4; He, Hui3; Chen, Kaifeng4; Chen, Shixin4; Lei, Hongtao1; Chen, Tie-Gen2; Ni, Shao-Fei3; Li, Zhaodong4 |
| 刊名 | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
 |
| 出版日期 | 2024-04-29 |
| 页码 | 10 |
| 关键词 | fluorine amino acid esters palladium nickel asymmetric synthesis |
| ISSN号 | 1433-7851 |
| DOI | 10.1002/anie.202402038 |
| 通讯作者 | Chen, Tie-Gen(chentiegen@simm.ac.cn) ; Ni, Shao-Fei(sfni@stu.edu.cn) ; Li, Zhaodong(scaulizhaodong@scau.edu.cn) |
| 英文摘要 | A novel enantioselective Tsuji-Trost-type cross coupling reaction between gem-difluorinated cyclopropanes and N-unprotected amino acid esters enabled by synergistic Pd/Ni/chiral aldehyde catalysis is presented herein. This transformation streamlined the diversity-oriented synthesis (DOS) of optically active alpha-quaternary alpha-amino acid esters bearing a linear 2-fluoroallylic motif, which served as an appealing platform for the construction of other valuable enantioenriched compounds. The key intermediates were confirmed by HRMS detection, while DFT calculations revealed that the excellent enantioselectivity was attributed to the stabilizing non-covalent interactions between the Pd(II)-pi-fluoroallyl species and the Ni(II)-Schiff base complex. |
| WOS关键词 | STEREODIVERGENT SYNTHESIS ; SYNERGISTIC CATALYSIS ; ALKYLATION ; ALLYLATION ; ENABLES |
| 资助项目 | Guangdong Basic and Applied Basic Research Foundation ; National Key Research and Development Program of China[2023YFF1104700] ; National Key Research and Development Program of China[2021YFD1800600] ; National Natural Science Foundation of China[22001080] ; STU Scientific Research Foundation for Talents[NTF20022] ; [2021(A1515012433)] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:001214202400001 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/310867]  |
| 专题 | 中国科学院上海药物研究所 |
| 通讯作者 | Chen, Tie-Gen; Ni, Shao-Fei; Li, Zhaodong |
| 作者单位 | 1.South China Agr Univ, Guangdong Prov Key Lab Food Qual & Safety, Guangzhou 510642, Peoples R China 2.Chinese Acad Sci, Zhongshan Inst Drug Discovery, Shanghai Inst Mat Med, Guangzhou 528400, Guangdong, Peoples R China 3.Shantou Univ, Dept Chem, Shantou 515063, Guangdong, Peoples R China 4.South China Agr Univ, Natl Key Lab Green Pesticide, Minist Educ, Guangzhou 510642, Peoples R China |
| 推荐引用方式 GB/T 7714 | Su, Zheng,Tan, Binhong,He, Hui,et al. Enantioselective Tsuji-Trost α-Fluoroallylation of Amino Acid Esters with Gem-Difluorinated Cyclopropanes[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2024:10. |
| APA | Su, Zheng.,Tan, Binhong.,He, Hui.,Chen, Kaifeng.,Chen, Shixin.,...&Li, Zhaodong.(2024).Enantioselective Tsuji-Trost α-Fluoroallylation of Amino Acid Esters with Gem-Difluorinated Cyclopropanes.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,10. |
| MLA | Su, Zheng,et al."Enantioselective Tsuji-Trost α-Fluoroallylation of Amino Acid Esters with Gem-Difluorinated Cyclopropanes".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2024):10. |
入库方式： OAI收割
来源：上海药物研究所
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