title: Catalyzed addition of diazoacetoacetates to imines: synthesis of highly functionalized aziridines.
abstract: The addition of diazoacetoacetates to aromatic imines derived from p-methoxyaniline is achieved using dirhodium tetraacetate as the catalyst. Highly functionalized aziridines are obtained in good yield and with excellent stereoselectivity. 2-Diazo-1,3-diketones also provide good yields of aziridines, but dimethyl diazomalonate is inactive in the transformation. The diazoacetoacetates of chiral alcohols are also examined in the reaction and moderate diastereoselectivity is achieved with (R)-pantolactone-derived diazoacetoacetate. A reaction mechanism through metal-carbene and azomethine ylide is proposed.
authors.affiliation: Industrial Institute of Fine Chemicals and Synthetic Drugs, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510080, China.
authors.forename: Xue-jing
authors.initials: XJ
authors.lastname: Zhang
authors.forename: Ming
authors.initials: M
authors.lastname: Yan
authors.forename: Dan
authors.initials: D
authors.lastname: Huang
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D002563:Cerium / Q000737:chemistry; D015195:Drug Design; D004563:Electrochemistry / Q000379:methods; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D008670:Metals / Q000737:chemistry; D008968:Molecular Conformation; D009566:Nitrates / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000737:chemistry
chemical_list: D000438:Alcohols; D000596:Amino Acids; D001388:Aziridines; D001391:Azo Compounds; D007097:Imines; D008670:Metals; D009566:Nitrates; D013882:Thiosemicarbazones; C512188:azomethine; D002563:Cerium; D002244:Carbon; D012238:Rhodium; C006568:ammonium nitrate