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

Wang, Fangyuan1; Zhang, Zongpeng1; Chen, Yu1; Ratovelomanana-Vidal, Virginie2; Yu, Peiyuan1; Chen, Gen-Qiang3; Zhang, Xumu1

2022-12-17

10.1038/s41467-022-35124-5

NATURE COMMUNICATIONS   Impact Factor & Quartile

2041-1723

["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."]

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First ; Corresponding

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]

Science & Technology - Other Topics

Multidisciplinary Sciences

WOS:000936998100013

NATURE PORTFOLIO

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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

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).

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).

Wang, Fangyuan,et al."Stereodivergent synthesis of chiral succinimides via Rh-catalyzed asymmetric transfer hydrogenation".NATURE COMMUNICATIONS 13.1(2022).