Organocatalyzed Sulfa-Michael Addition of Thiophenols on Trisubstituted α-Fluoroacrylates, a Straightforward Access to Chiral Fluorinated Compounds
Résumé
In this manuscript, a simple and efficient sulfa-Michael addition reaction of aryl thiols to trisubstituted α-fluoro-α,β-unsaturated esters both in racemic and, for the first time, in enantioselective version is reported. The commercially available dimer of cinchona derivatives (DHQ)2PYR was used as catalyst. This strategy showed a great tolerance for various substrates and substituents, providing fair to excellent yields, moderate to excellent diastereoselectivities (2:1 to > 99:1) and low to good enantioselectivities (2 to 87%). The reaction has been applied to the synthesis of fluorinated analogues of Diltiazem and Tiazesim, both therapeutic agents.
Domaines
ChimieOrigine | Fichiers produits par l'(les) auteur(s) |
---|