Diastereo- and Enantioselective Synthesis of Tetracyclic Cycloheptanols through (4+3) Annulation via C-C/C-H Activation Cascade
© 2023 Wiley-VCH GmbH..
Transition metal-catalyzed annulations of four-membered rings via C-C activation are powerful tools to construct complex fused and bridged ring systems. Despite significant progress in (4+1), (4+2) and (4+4) annulations, the (4+3) annulation remains unexplored. Herein, we develop an asymmetric Rh-catalyzed intramolecular (4+3) annulation of α-arylalkene-tethered benzocyclobutenols for the synthesis of dihydrofuran-annulated dibenzocycloheptanols with two discontinuous chiral carbon centers via a C-C and C-H activation cascade. The reaction features excellent diastereo- and enantioselectivities and 100 % atom economy, and is applicable to late-stage modification of complex molecules.
| 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), 13 vom: 22. März, Seite e202317433 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Yan, Xin [VerfasserIn] |
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| Links: |
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| Themen: |
(4+3) Annulation |
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| Anmerkungen: |
Date Revised 18.03.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1002/anie.202317433 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM365775045 |
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| 520 | |a Transition metal-catalyzed annulations of four-membered rings via C-C activation are powerful tools to construct complex fused and bridged ring systems. Despite significant progress in (4+1), (4+2) and (4+4) annulations, the (4+3) annulation remains unexplored. Herein, we develop an asymmetric Rh-catalyzed intramolecular (4+3) annulation of α-arylalkene-tethered benzocyclobutenols for the synthesis of dihydrofuran-annulated dibenzocycloheptanols with two discontinuous chiral carbon centers via a C-C and C-H activation cascade. The reaction features excellent diastereo- and enantioselectivities and 100 % atom economy, and is applicable to late-stage modification of complex molecules | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a (4+3) Annulation | |
| 650 | 4 | |a Benzocyclobutenols | |
| 650 | 4 | |a Cascade Reaction | |
| 650 | 4 | |a C−C Activation | |
| 650 | 4 | |a Selective Synthesis | |
| 700 | 1 | |a Liu, Min |e verfasserin |4 aut | |
| 700 | 1 | |a Pan, Deng |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Qi |e verfasserin |4 aut | |
| 700 | 1 | |a Tang, Qi |e verfasserin |4 aut | |
| 700 | 1 | |a Dai, Ya-Mei |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 Huang, Genping |e verfasserin |4 aut | |
| 700 | 1 | |a Song, Feijie |e verfasserin |4 aut | |
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