Palladium-Catalyzed Asymmetric Decarboxylation of 5-Vinyloxazolidine-2,4-Diones Triggering the Dearomatization of Electron-Deficient Indoles for the Synthesis of Chiral Highly Functionalized Pyrroloindolines
A catalyst system consisting of a chiral phosphoramidite ligand and Pd2(dba)3·CHCl3 causes the decarboxylation of 5-vinyloxazolidine-2,4-diones to generate amide-containing aza-π-allylpalladium 1,3-dipole intermediates, which are capable of triggering the dearomatization of 3-nitroindoles for diastereo- and enantioselective [3+2] cycloaddition, leading to the formation of a series of highly functionalized pyrroloindolines containing three contiguous stereogenic centers with excellent results (up to 99% yield, 88:12 dr, and 96% ee).
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:26 |
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| Enthalten in: |
Organic letters - 26(2024), 15 vom: 19. Apr., Seite 3310-3315 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Dou, Pei-Hao [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Revised 19.04.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/acs.orglett.4c01003 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM370767489 |
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| 245 | 1 | 0 | |a Palladium-Catalyzed Asymmetric Decarboxylation of 5-Vinyloxazolidine-2,4-Diones Triggering the Dearomatization of Electron-Deficient Indoles for the Synthesis of Chiral Highly Functionalized Pyrroloindolines |
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| 500 | |a Date Revised 19.04.2024 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a A catalyst system consisting of a chiral phosphoramidite ligand and Pd2(dba)3·CHCl3 causes the decarboxylation of 5-vinyloxazolidine-2,4-diones to generate amide-containing aza-π-allylpalladium 1,3-dipole intermediates, which are capable of triggering the dearomatization of 3-nitroindoles for diastereo- and enantioselective [3+2] cycloaddition, leading to the formation of a series of highly functionalized pyrroloindolines containing three contiguous stereogenic centers with excellent results (up to 99% yield, 88:12 dr, and 96% ee) | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Fu, Xiao-Hui |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Yan |e verfasserin |4 aut | |
| 700 | 1 | |a Ge, Zhen-Zhen |e verfasserin |4 aut | |
| 700 | 1 | |a Zhou, Ming-Qiang |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Zhen-Hua |e verfasserin |4 aut | |
| 700 | 1 | |a You, Yong |e verfasserin |4 aut | |
| 700 | 1 | |a Yang, Lei |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Yan-Ping |e verfasserin |4 aut | |
| 700 | 1 | |a Zhao, Jian-Qiang |e verfasserin |4 aut | |
| 700 | 1 | |a Yuan, Wei-Cheng |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Organic letters |d 1999 |g 26(2024), 15 vom: 19. Apr., Seite 3310-3315 |w (DE-627)NLM106817639 |x 1523-7052 |7 nnns |
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