Catalyzed addition of diazoacetoacetates to imines: synthesis of highly functionalized aziridines.
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.
Zhang
Xue-jing
XJ
Industrial Institute of Fine Chemicals and Synthetic Drugs, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510080, China.
Yan
Ming
M
Huang
Dan
D
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
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