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Journal articles
N‐Heterocyclic Carbene‐Catalyzed Formal [6+2] Annulation Reaction via Cross‐Conjugated Aza‐Trienolate Intermediates
Abstract : The diverse reactivity of N‐heterocyclic carbenes (NHCs) in organocatalysis is due to the possibility of different modes of action. Although NHC‐bound enolates and dienolates are known, the related NHC‐bound cross‐conjugated aza‐trienolates remain elusive. Herein, we demonstrate the NHC‐catalyzed formal [6+2] annulation of nitrogen‐containing heterocyclic aldehydes with α,α,α‐trifluoroacetophenones leading to the formation of versatile pyrrolooxazolones (29 examples). The catalytically generated cross‐conjugated aza‐trienolates (aza‐fulvene type) underwent smooth [6+2] annulation with electrophilic ketones to afford the product in moderate to good yields under mild conditions. Preliminary DFT studies on the mechanism are also provided.
https://hal-normandie-univ.archives-ouvertes.fr/hal-02455771
Contributor : Tatiana Besset <>
Submitted on : Tuesday, December 8, 2020 - 10:10:56 AM
Last modification on : Tuesday, December 15, 2020 - 8:50:55 AM
Contributor : Tatiana Besset <>
Submitted on : Tuesday, December 8, 2020 - 10:10:56 AM
Last modification on : Tuesday, December 15, 2020 - 8:50:55 AM
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