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DNA‐Based Asymmetric Inverse Electron‐Demand Hetero‐Diels–Alder
Author(s) -
Mansot Justine,
Lauberteaux Jimmy,
Lebrun Aurélien,
Mauduit Marc,
Vasseur JeanJacques,
Marcia de Figueiredo Renata,
Arseniyadis Stellios,
Campagne JeanMarc,
Smietana Michael
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202000516
Subject(s) - stereocenter , inverse , catalysis , diels–alder reaction , bicyclic molecule , chemistry , combinatorial chemistry , enantioselective synthesis , stereochemistry , organic chemistry , mathematics , geometry
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.