DNA‐Based Asymmetric Inverse Electron‐Demand Hetero‐Diels–Alder - Université de Montpellier Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2020

DNA‐Based Asymmetric Inverse Electron‐Demand Hetero‐Diels–Alder

Marc Mauduit
Stellios Arseniyadis


While artificial cyclases hold great promise in chemical synthesis, this work presents the first example of a DNA-catalyzed inverse electron-demand hetero-Diels-Alder (IEDHDA) between dihydrofuran and various α,β-unsaturated acyl imidazoles. The resulting fused bicyclic O,O-acetals containing three contiguous stereogenic centers are obtained in high yields (up to 99 %) and excellent diastereo- (up to >99:1 dr) and enantioselectivities (up to 95 % ee) using a low catalyst loading. Most importantly, these results show that the concept of DNA-based asymmetric catalysis can be expanded to new synthetic transformations offering an efficient, sustainable, and highly selective tool for the construction of chiral building blocks.
Fichier principal
Vignette du fichier
Mansot-2020-DNA-Based Asymmetric Inverse Electron-Demand Hetero-Diels-Alder (1).pdf (1.9 Mo) Télécharger le fichier
Origine Fichiers produits par l'(les) auteur(s)

Dates et versions

hal-02512892 , version 1 (16-04-2020)



Justine Mansot, Jimmy Lauberteaux, Aurélien Lebrun, Marc Mauduit, Jean-Jacques Vasseur, et al.. DNA‐Based Asymmetric Inverse Electron‐Demand Hetero‐Diels–Alder. Chemistry - A European Journal, 2020, 26 (16), pp.3519-3523. ⟨10.1002/chem.202000516⟩. ⟨hal-02512892⟩
180 Consultations
239 Téléchargements



Gmail Mastodon Facebook X LinkedIn More