Acyl-Imidazoles A Privileged Ester Surrogate for Enantioselective Synthesis

J. Lauberteaux (1) , D. Pichon (2) , Olivier Baslé (3) , Marc Mauduit (2) , Renata Marcia de Figueiredo (1) , J.-M. Campagne (1)

1 ICGM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier
2 ISCR - Institut des Sciences Chimiques de Rennes
3 LCC - Laboratoire de chimie de coordination

Since the first report by Evans in asymmetric Friedel‐Crafts reactions, the use of acyl‐imidazoles 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: α‐(enolate chemistry), β‐(conjugate additions), α,β‐(cycloadditions) or γ/δ‐(vinylogous). An overview of the contemporary and growing interest in acyl‐imidazoles in metal‐ and organo‐catalyzed transformations (bio‐hybrid catalytic systems will be fully described in a back‐to‐back Minireview) will be highlighted. Moreover, post‐functionalization expediencies are also going to be discussed in this Minireview.

Keywords: post-functionalizations; catalysis; asymmetric synthesis; versatile substrates; acyl-imidazoles

Domains: Chemical Sciences

J. Lauberteaux, D. Pichon, Olivier Baslé, Marc Mauduit, Renata Marcia de Figueiredo, et al.. Acyl-Imidazoles A Privileged Ester Surrogate for Enantioselective Synthesis. ChemCatChem, 2019, 11 (23), pp.5705-5722. ⟨10.1002/cctc.201900754⟩. ⟨hal-02181832⟩