DNA-Based Asymmetric Inverse Electron-Demand Hetero-Diels–Alder |
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Authors: | Justine Mansot Jimmy Lauberteaux Aurélien Lebrun Marc Mauduit Dr Jean-Jacques Vasseur Dr Renata Marcia de Figueiredo Dr Stellios Arseniyadis Prof Dr Jean-Marc Campagne Prof Dr Michael Smietana |
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Institution: | 1. Institut des Biomolécules Max Mousseron, Université de Montpellier, CNRS, ENSCM, Place Eugène Bataillon, 34095 Montpellier, France;2. Institut Charles Gerhardt, CNRS, Université de Montpellier, ENSCM, Avenue Emile Jeanbrau, 34296 Montpellier, France;3. Ecole Nationale Supérieure de Chimie de Rennes, CNRS, ISCR UMR 6226, Univ Rennes, 35000 Rennes, France;4. School of Biological and Chemical Sciences, Queen Mary University of London, Mile End Road, London, E1 4NS UK |
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Abstract: | 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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Keywords: | [4+2] cycloaddition biohybrid catalysis copper DNA inverse electron-demand hetero-Diels–Alder |
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