Article Dans Une Revue European Journal of Organic Chemistry Année : 2020

Endocyclic Enamides Derived from Aza‐Diketopiperazines as Olefin Partners in Povarov Reaction: An Access to Tetracyclic N‐Heterocycles

Résumé

Original endocyclic enamides based on a bicyclic aza-diketopiperazine (aza-DKP) structure have been used as dienophile partners in the Povarov reaction. The reported method represents a successful strategy for the structural diversification of the aza-DKP scaffold, giving access to a new family of fused tetracyclic N-heterocycles, which contain at least four nitrogen atoms in the heterocyclic structure. Depending on the nature of the aldehyde partner, the cycloadditions have been performed either as a two-component or a three-component Povarov reaction (2CPR or 3CPR), in the presence of BF3 as a Lewis acid catalyst. With aliphatic aldehydes the reaction proceeds with high diastereoselectivities in favor of the cis compounds. Some mechanistic aspects of this cycloaddition have been examined computationally

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hal-03441064 , version 1 (22-11-2021)

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Timothé Maujean, Isabelle Chataigner, Nicolas Girard, Mihaela Gulea, Dominique Bonnet. Endocyclic Enamides Derived from Aza‐Diketopiperazines as Olefin Partners in Povarov Reaction: An Access to Tetracyclic N‐Heterocycles. European Journal of Organic Chemistry, 2020, 2020 (47), pp.7385-7395. ⟨10.1002/ejoc.202001339⟩. ⟨hal-03441064⟩
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