Enantioselective addition of thioacetic acid to nitroalkenes via N-sulfinyl urea organocatalysis.
The highly enantioselective addition of thioacetic acid to nitroalkenes using a new sulfinyl urea organocatalyst is described. The addition of thioacetic acid proceeds in high yields and enantioselectivities for a variety of aromatic and aliphatic nitroalkene substrates. This new method is useful for preparing chiral 1,2-aminothiol derivatives, as demonstrated by the first enantioselective synthesis of the clinically used antifungal drug sulconazole.
Kimmel
Kyle L
KL
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Robak
MaryAnn T
MT
Ellman
Jonathan A
JA
D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013457:Sulfur Compounds / Q000138:chemical synthesis / Q000737:chemistry; D014508:Urea / Q000138:chemical synthesis / Q000737:chemistry*
D000475:Alkenes; D000935:Antifungal Agents; D007093:Imidazoles; D009574:Nitro Compounds; D013438:Sulfhydryl Compounds; D013457:Sulfur Compounds; C033308:sulconazole; D014508:Urea; C005732:thioacetic acid