Construction of Bridged Benzazepines via Photo-Induced Dearomatization
© 2023 Wiley-VCH GmbH..
Bridged benzazepine scaffolds, possessing unique structural and physicochemical activities, are widespread in various natural products and drugs. The construction of these skeletons often requires elaborate synthetic effort with low efficiency. Herein, we develop a simple and divergent approach for constructing various bridged benzazepines by a photocatalytic intermolecular dearomatization of naphthalene derivatives with readily available α-amino acids. The bridged motif is created via a cascade sequence involving photocatalytic 1,4-hydroaminoalkylation, alkene isomerization and cyclization. Interestingly, the diastereoselectivity can be regulated through different reaction modes in the cyclization step. Moreover, aminohydroxylation and its further bromination have also been demonstrated to access highly functionalized bridged benzazepines. Preliminary mechanistic studies have been performed to get insights into the mechanism. This method provides a divergent synthetic approach for construction of highly functionalized bridged benzazepines, which have been otherwise difficult to access.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:63 |
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| Enthalten in: |
Angewandte Chemie (International ed. in English) - 63(2024), 2 vom: 08. Jan., Seite e202314304 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Song, Ting-Ting [VerfasserIn] |
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| Links: |
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| Themen: |
Amino Acids |
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| Anmerkungen: |
Date Revised 05.01.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1002/anie.202314304 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 520 | |a Bridged benzazepine scaffolds, possessing unique structural and physicochemical activities, are widespread in various natural products and drugs. The construction of these skeletons often requires elaborate synthetic effort with low efficiency. Herein, we develop a simple and divergent approach for constructing various bridged benzazepines by a photocatalytic intermolecular dearomatization of naphthalene derivatives with readily available α-amino acids. The bridged motif is created via a cascade sequence involving photocatalytic 1,4-hydroaminoalkylation, alkene isomerization and cyclization. Interestingly, the diastereoselectivity can be regulated through different reaction modes in the cyclization step. Moreover, aminohydroxylation and its further bromination have also been demonstrated to access highly functionalized bridged benzazepines. Preliminary mechanistic studies have been performed to get insights into the mechanism. This method provides a divergent synthetic approach for construction of highly functionalized bridged benzazepines, which have been otherwise difficult to access | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Amino Acids | |
| 650 | 4 | |a Dearomatization | |
| 650 | 4 | |a Heterocylces | |
| 650 | 4 | |a Photocatalysis | |
| 650 | 4 | |a Synthetic Methods | |
| 700 | 1 | |a Mei, Yong-Kang |e verfasserin |4 aut | |
| 700 | 1 | |a Liu, Yan |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Xiao-Yu |e verfasserin |4 aut | |
| 700 | 1 | |a Guo, Shi-Yu |e verfasserin |4 aut | |
| 700 | 1 | |a Ji, Ding-Wei |e verfasserin |4 aut | |
| 700 | 1 | |a Wan, Boshun |e verfasserin |4 aut | |
| 700 | 1 | |a Yuan, Weiming |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Qing-An |e verfasserin |4 aut | |
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