title: Enantioselective addition of thioacetic acid to nitroalkenes via N-sulfinyl urea organocatalysis.
abstract: 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.
authors.affiliation: Department of Chemistry, University of California, Berkeley, California 94720, USA.
authors.forename: Kyle L
authors.initials: KL
authors.lastname: Kimmel
authors.forename: MaryAnn T
authors.initials: MT
authors.lastname: Robak
authors.forename: Jonathan A
authors.initials: JA
authors.lastname: Ellman
mesh_terms: 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*
chemical_list: D000475:Alkenes; D000935:Antifungal Agents; D007093:Imidazoles; D009574:Nitro Compounds; D013438:Sulfhydryl Compounds; D013457:Sulfur Compounds; C033308:sulconazole; D014508:Urea; C005732:thioacetic acid