N‑Heterocyclic Carbene-Catalyzed Formal Intramolecular [3 + 2] Annulations of Cyclohexadienone-Tethered Ynals

N‑Heterocyclic Carbene-Catalyzed Formal Intramolecular [3 + 2] Annulations of Cyclohexadienone-Tethered Ynals

A formal [3 + 2] annulation of cyclohexadienone-tethered ynals is enabled by an N-heterocyclic carbene (NHC) catalyst, affording a tricyclo­[6.2.1.04,11]­undecane framework. This study represents the first demonstration of using CC double bonds as the reaction partner in the NHC-catalyzed annulatio...

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Veröffentlicht in:Organic letters 2024-05, Vol.26 (17), p.3552-3556
Hauptverfasser: Wang, Ya-Jie, Kang, Wen-Yu, Zhao, Yi-Wen, Wang, Yu-Hui, Tian, Ping
Format: Artikel
Sprache:eng
Schlagworte:
carbenes
catalysts
catalytic activity
heterocyclic nitrogen compounds
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Zusammenfassung:A formal [3 + 2] annulation of cyclohexadienone-tethered ynals is enabled by an N-heterocyclic carbene (NHC) catalyst, affording a tricyclo­[6.2.1.04,11]­undecane framework. This study represents the first demonstration of using CC double bonds as the reaction partner in the NHC-catalyzed annulation of ynals. This strategy is characterized by mild reaction conditions and 100% atom economy as well as high catalytic performance and efficiency.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c00950