3 research outputs found
Acyl-Imidazoles A Privileged Ester Surrogate for Enantioselective Synthesis
International audienceSince the first report by Evans in asymmetric FriedelâCrafts reactions, the use of acylâimidazoles has blossomed as powerful ester/amide surrogates. The imidazole scaffold indeed displays stability and special activation features allowing both better reactivity and selectivity in traditional ester/amide functionalizations: αâ(enolate chemistry), ÎČâ(conjugate additions), α,ÎČâ(cycloadditions) or Îł/ÎŽâ(vinylogous). An overview of the contemporary and growing interest in acylâimidazoles in metalâ and organoâcatalyzed transformations (bioâhybrid catalytic systems will be fully described in a backâtoâback Minireview) will be highlighted. Moreover, postâfunctionalization expediencies are also going to be discussed in this Minireview
DNA-Based Asymmetric Inverse Electron-Demand Hetero-Diels-Alder
International audienceWhile 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,ÎČ-unsaturated acyl imidazoles. The resulting fused bicyclic O,O-acetals containing three contiguous stereogenic centers are obtained in high yields (up to 99â%) and excellent diastereo- (up to >99:1 dr) and enantioselectivities (up to 95â% 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