| Title | Rhodium-Catalyzed Chemo-, Regio- and Enantioselective Hydroformylation of Cyclopropyl-Functionalized Trisubstituted Alkenes |
| Author | |
| Corresponding Author | Zhang，Xumu |
| Publication Years | 2022-07-01
|
| DOI | |
| Source Title | |
| ISSN | 1433-7851
|
| EISSN | 1521-3773
|
| Volume | 61 |
| Abstract | The first rhodium-catalyzed highly chemo-, regio- and enantioselective hydroformylation of cyclopropyl-functionalized trisubstituted alkenes affording useful chiral cyclopropyl entities is reported. Compared to generally used diphosphine ligands for asymmetric catalysis, the modified hybrid phosphorus ligand, named (R,S)-DTBM-Yanphos, can convert a series of readily available cyclopropyl-functionalized trisubstituted alkenes into high-value chiral cyclopropyl-functionalized aldehydes with high selectivities (81-98 % ee). Gram-scale reactions (TON up to 1500) and follow-up transformations to the corresponding alcohol, acid, esters and nitrile are also presented. Finally, a possible hydroformylation mechanism involving ring-open-hydroformylation pathways is proposed based on control and deuteroformylation reactions. |
| Keywords | |
| URL | [Source Record] |
| Indexed By | |
| Language | English
|
| Important Publications | NI Journal Papers
|
| SUSTech Authorship | First
; Corresponding
|
| Funding Project | Guangdong Provincial Key Laboratory of Catalysis[2020B121201002]
; Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis[ZDSYS20190902093215877]
; Guangdong Basic and Applied Basic Research Foundation[2021A1515110808]
; National Natural Science Foundation of China[21991113]
|
| WOS Research Area | Chemistry
|
| WOS Subject | Chemistry, Multidisciplinary
|
| WOS Accession No | WOS:000822836500001
|
| Publisher | |
| EI Accession Number | 20222812344919
|
| EI Keywords | Catalysis
; Enantioselectivity
; Ligands
; Olefins
|
| ESI Classification Code | Physical Chemistry:801.4
; Chemical Reactions:802.2
; Chemical Operations:802.3
; Organic Compounds:804.1
|
| ESI Research Field | CHEMISTRY
|
| Data Source | Web of Science
|
| Citation statistics |
Cited Times [WOS]:5
|
| Document Type | Journal Article |
| Identifier | http://kc.sustech.edu.cn/handle/2SGJ60CL/355937 |
| Department | Department of Chemistry 前沿与交叉科学研究院 |
| Affiliation | 1.Department of Chemistry and Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis,Southern University of Science and Technology,Shenzhen,1088 Xueyuan Road,518055,China 2.Academy for Advanced Interdisciplinary Studies and Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,1088 Xueyuan Road,518055,China |
| First Author Affilication | Department of Chemistry |
| Corresponding Author Affilication | Department of Chemistry; Academy for Advanced Interdisciplinary Studies |
| First Author's First Affilication | Department of Chemistry |
| Recommended Citation GB/T 7714 |
Li，Shuailong,Zhang，Dequan,Zhang，Runtong,et al. Rhodium-Catalyzed Chemo-, Regio- and Enantioselective Hydroformylation of Cyclopropyl-Functionalized Trisubstituted Alkenes[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2022,61.
|
| APA |
Li，Shuailong,Zhang，Dequan,Zhang，Runtong,Bai，Shao Tao,&Zhang，Xumu.(2022).Rhodium-Catalyzed Chemo-, Regio- and Enantioselective Hydroformylation of Cyclopropyl-Functionalized Trisubstituted Alkenes.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,61.
|
| MLA |
Li，Shuailong,et al."Rhodium-Catalyzed Chemo-, Regio- and Enantioselective Hydroformylation of Cyclopropyl-Functionalized Trisubstituted Alkenes".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 61(2022).
|
| Files in This Item: | ||||||
| File Name/Size | DocType | Version | Access | License | ||
| Angew Chem Int Ed - （1408KB） | Restricted Access | -- | ||||
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