Highly enantioselective synthesis of beta-amidophenylthioethers by organocatalytic desymmetrization of meso-aziridines.
The desymmetrization of N-acylaziridines with Me(3)SiSPh, catalyzed by commercially available (R) and (S)-VAPOL hydrogen phosphate, produced beta-(N-acylamino)phenylthioethers in a highly enantioselective and efficient manner (78-99% ee). The selection of the suitable aziridine/nucleophile/catalyst molar ratio is crucial to obtain high ee's.
Della Sala
Giorgio
G
Department of Chemistry, University of Salerno, Via Ponte Don Melillo 8, 84024 Fisciano (SA), Italy. gdsala@unisa.it
Lattanzi
Alessandra
A
D001388:Aziridines / Q000737:chemistry*; D010616:Phenanthrenes / Q000737:chemistry*; D013237:Stereoisomerism; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry
D001388:Aziridines; D010616:Phenanthrenes; D013440:Sulfides; C510253:VAPOL ligand