| Title | Chiral Phosphine Catalyzed Allylic Alkylation of Benzylidene Succinimides with Morita-Baylis-Hillman Carbonates |
| Author | |
| Corresponding Author | Sun, Jianwei; Li, Pengfei |
| Publication Years | 2023-03-01
|
| DOI | |
| Source Title | |
| EISSN | 1420-3049
|
| Volume | 28Issue:6 |
| Abstract | Owing to their unique chemical properties, alpha-alkylidene succinimides generally act as versatile synthons in organic synthesis. Compared with well-established annulations, nucleophilic alkylations of alpha-alkylidene succinimides are very limited. Accordingly, an organocatalytic allylic alkylation of alpha-benzylidene succinimides with Morita-Baylis-Hillman (MBH) carbonates was established. In the presence of a chiral phosphine catalyst, alpha-benzylidene succinimides reacted smoothly with MBH carbonates under mild conditions to furnish a series of optical active succinimides in high yields and enantioselectivities. Different from the reported results, the organocatalytic enantioselective construction of pyrrolidine-2,5-dione frameworks bearing contiguous chiral tertiary carbon centers was achieved via this synthetic strategy. Scaling up the reaction indicated that it is a practical strategy for the organocatalytic enantioselective alkylation of alpha-alkylidene succinimides. A possible reaction mechanism was also proposed. |
| Keywords | |
| URL | [Source Record] |
| Indexed By | |
| Language | English
|
| SUSTech Authorship | First
; Corresponding
|
| Funding Project | National Natural Science Foundation of China[21871128]
; Guangdong Innovative Program[2019BT02Y335]
|
| WOS Research Area | Biochemistry & Molecular Biology
; Chemistry
|
| WOS Subject | Biochemistry & Molecular Biology
; Chemistry, Multidisciplinary
|
| WOS Accession No | WOS:000960091900001
|
| Publisher | |
| ESI Research Field | CHEMISTRY
|
| Data Source | Web of Science
|
| Citation statistics |
Cited Times [WOS]:0
|
| Document Type | Journal Article |
| Identifier | http://kc.sustech.edu.cn/handle/2SGJ60CL/524015 |
| Department | Department of Chemistry 深圳格拉布斯研究院 |
| Affiliation | 1.Southern Univ Sci & Technol SUSTech, Shenzhen Grubbs Inst, Coll Sci, Dept Chem,Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China 2.Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Clear Water Bay, Hong Kong, Peoples R China 3.Southern Univ Sci & Technol, Guangming Adv Res Inst, Shenzhen 518055, Peoples R China |
| First Author Affilication | Department of Chemistry; Shenzhen Grubbs Institute; Southern University of Science and Technology |
| Corresponding Author Affilication | Department of Chemistry; Shenzhen Grubbs Institute; Southern University of Science and Technology |
| First Author's First Affilication | Department of Chemistry; Shenzhen Grubbs Institute |
| Recommended Citation GB/T 7714 |
Liu, Chang,Sun, Jianwei,Li, Pengfei. Chiral Phosphine Catalyzed Allylic Alkylation of Benzylidene Succinimides with Morita-Baylis-Hillman Carbonates[J]. MOLECULES,2023,28(6).
|
| APA |
Liu, Chang,Sun, Jianwei,&Li, Pengfei.(2023).Chiral Phosphine Catalyzed Allylic Alkylation of Benzylidene Succinimides with Morita-Baylis-Hillman Carbonates.MOLECULES,28(6).
|
| MLA |
Liu, Chang,et al."Chiral Phosphine Catalyzed Allylic Alkylation of Benzylidene Succinimides with Morita-Baylis-Hillman Carbonates".MOLECULES 28.6(2023).
|
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