中文版 | English
Title

Stereodivergent synthesis of chiral succinimides via Rh-catalyzed asymmetric transfer hydrogenation

Author
Corresponding AuthorYu, Peiyuan; Chen, Gen-Qiang; Zhang, Xumu
Publication Years
2022-12-17
DOI
Source Title
EISSN
2041-1723
Volume13Issue:1
Abstract
["Chiral succinimides are ubiquitous in bioactive compounds. Here, authors report a stereodivergent method for accessing 3,4-disubstituted succinimides, and the origin of stereoselectivity is elucidated by experimental and theoretical investigations.","Chiral succinimide moieties are ubiquitous in biologically active natural products and pharmaceuticals. Until today, despite the great interest, little success has been made for stereodivergent synthesis of chiral succinimides. Here, we report a general and efficient method for accessing 3,4-disubstituted succinimides through a dynamic kinetic resolution strategy based on asymmetric transfer hydrogenation. The Rh catalyst system exhibit high activities, enantioselectivities, and diastereoselectivities (up to 2000 TON, up to >99% ee, and up to >99:1 dr). Products with syn- and anti-configuration are obtained separately by control of the reaction conditions. For the N-unprotected substrates, both the enol and the imide group can be reduced by control of reaction time and catalyst loading. In addition, the detailed reaction pathway and origin of stereoselectivity are elucidated by control experiments and theoretical calculations. This study offers a straightforward and stereodivergent approach to the valuable enantioenriched succinimides (all 4 stereoisomers) from cheap chemical feedstocks in a single reaction step."]
URL[Source Record]
Indexed By
Language
English
SUSTech Authorship
First ; Corresponding
Funding Project
National Key R&D Program of China[2021YFA1500201] ; Shenzhen Nobel Prize Scientists Laboratory Project[C17213101] ; Key-Area Research and Development Program of Guangdong Province[2020B010188001] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002] ; Innovative Team of Universities in Guangdong Province[2020KCXTD016] ; National Natural Science Foundation of China["21901107","22171129","21991113"] ; Guangdong Basic and Applied Basic Research Foundation[2022B1515020055] ; Shenzhen Science and Technology Innovation Committee[JCYJ20210324104202007]
WOS Research Area
Science & Technology - Other Topics
WOS Subject
Multidisciplinary Sciences
WOS Accession No
WOS:000936998100013
Publisher
Data Source
Web of Science
Citation statistics
Cited Times [WOS]:1
Document TypeJournal Article
Identifierhttp://kc.sustech.edu.cn/handle/2SGJ60CL/501420
DepartmentDepartment of Chemistry
前沿与交叉科学研究院
深圳格拉布斯研究院
Affiliation
1.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Dept Chem, Shenzhen 518000, Peoples R China
2.PSL Univ, Chim ParisTech, CNRS, Inst Chem life & Hlth Sci 1,Team CSB2D, Inst, F-75005 Paris, France
3.Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, Shenzhen 518000, Peoples R China
First Author AffilicationDepartment of Chemistry;  Shenzhen Grubbs Institute
Corresponding Author AffilicationDepartment of Chemistry;  Shenzhen Grubbs Institute;  Academy for Advanced Interdisciplinary Studies
First Author's First AffilicationDepartment of Chemistry;  Shenzhen Grubbs Institute
Recommended Citation
GB/T 7714
Wang, Fangyuan,Zhang, Zongpeng,Chen, Yu,et al. Stereodivergent synthesis of chiral succinimides via Rh-catalyzed asymmetric transfer hydrogenation[J]. NATURE COMMUNICATIONS,2022,13(1).
APA
Wang, Fangyuan.,Zhang, Zongpeng.,Chen, Yu.,Ratovelomanana-Vidal, Virginie.,Yu, Peiyuan.,...&Zhang, Xumu.(2022).Stereodivergent synthesis of chiral succinimides via Rh-catalyzed asymmetric transfer hydrogenation.NATURE COMMUNICATIONS,13(1).
MLA
Wang, Fangyuan,et al."Stereodivergent synthesis of chiral succinimides via Rh-catalyzed asymmetric transfer hydrogenation".NATURE COMMUNICATIONS 13.1(2022).
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