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Article Dans Une Revue Chemistry - A European Journal Année : 2020

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

Marc Mauduit
Stellios Arseniyadis

Résumé

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.
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Dates et versions

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

Identifiants

Citer

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⟩
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