title: Organocatalytic asymmetric Neber reaction for the synthesis of 2H-azirine carboxylic esters.
abstract: The first enantioselective Neber reaction of β-ketoxime sulfonates catalyzed by a bifunctional thiourea has been developed. The reaction proceeds stereoselectively with 5 mol % of the catalyst to give the 2H-azirine carboxylic esters in good yields with up to 93% ee. In addition, the resulting azirines can be successfully employed in the stereoselective synthesis of di- and trisubstituted aziridines.
authors: Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
authors: Shota
authors: S
authors: Sakamoto
authors: Tsubasa
authors: T
authors: Inokuma
authors: Yoshiji
authors: Y
authors: Takemoto
mesh_terms: D001388:Aziridines / Q000138:chemical synthesis / Q000737:chemistry; D001389:Azirines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004952:Esters; D015394:Molecular Structure; D010091:Oximes / Q000737:chemistry; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
chemical_list: D001388:Aziridines; D001389:Azirines; D004952:Esters; D010091:Oximes; D013890:Thiourea