Modular Synthesis of Enantioenriched α-Chiral Homoallylic Amidines Enabled by Relay Ir/Cu Catalysis
The cascade of Ir-catalyzed enantioselective allylic amination and Cu-catalyzed alkyne-azide cycloaddition was designed for the asymmetric synthesis of homoallylic amidines. The nucleophilic addition of an in situ-generated enantioenriched tertiary allylamine to a ketenimine intermediate triggers a rapid and stereospecific zwitterionic aza-Claisen rearrangement in a 1,3-chiral transfer manner. The approach allows modular access to enantioenriched α-chiral homoallylic amidines in high yields with a high level of enantiomeric purity.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2022 |
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| Erschienen: |
2022 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:24 |
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| Enthalten in: |
Organic letters - 24(2022), 37 vom: 23. Sept., Seite 6783-6788 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Li, Ting-Peng [VerfasserIn] |
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| Links: |
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| Themen: |
48G762T011 |
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| Anmerkungen: |
Date Completed 26.09.2022 Date Revised 20.10.2022 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1021/acs.orglett.2c02655 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM345920783 |
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| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a The cascade of Ir-catalyzed enantioselective allylic amination and Cu-catalyzed alkyne-azide cycloaddition was designed for the asymmetric synthesis of homoallylic amidines. The nucleophilic addition of an in situ-generated enantioenriched tertiary allylamine to a ketenimine intermediate triggers a rapid and stereospecific zwitterionic aza-Claisen rearrangement in a 1,3-chiral transfer manner. The approach allows modular access to enantioenriched α-chiral homoallylic amidines in high yields with a high level of enantiomeric purity | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 7 | |a Alkynes |2 NLM | |
| 650 | 7 | |a Amidines |2 NLM | |
| 650 | 7 | |a Azides |2 NLM | |
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| 700 | 1 | |a Li, Ren-Sha |e verfasserin |4 aut | |
| 700 | 1 | |a Hu, Wei |e verfasserin |4 aut | |
| 700 | 1 | |a Xie, Jia-Xin |e verfasserin |4 aut | |
| 700 | 1 | |a Xu, Minghui |e verfasserin |4 aut | |
| 700 | 1 | |a Feng, Chun |e verfasserin |4 aut | |
| 700 | 1 | |a Ni, Hai-Liang |e verfasserin |4 aut | |
| 700 | 1 | |a Yu, Wen-Hao |e verfasserin |4 aut | |
| 700 | 1 | |a Hu, Ping |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Bi-Qin |e verfasserin |4 aut | |
| 700 | 1 | |a Cao, Peng |e verfasserin |4 aut | |
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