Component match in rhodium catalyzed three-component reactions of ethyl diazoacetate, H2O and aryl imines: a highly diastereoselective one-step synthesis of beta-aryl isoserine derivatives.
Water and ethyl diazoacetate were found to be matched components for generating highly reactive nucleophilic oxonium ylide in the presence of a dirhodium acetate catalyst. Simultaneous trapping of the oxonium ylide intermediate with aryl imines gave beta-aryl isoserine derivatives with high diastereoselectivity.
Guo
Zhenqiu
Z
Department of Chemistry, East China Normal University, Shanghai 200062, P. R. China.
Shi
Taoda
T
Jiang
Jun
J
Yang
Liping
L
Hu
Wenhao
W
D002384:Catalysis; D018360:Crystallography, X-Ray; D003979:Diazonium Compounds / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
D003979:Diazonium Compounds; D007097:Imines; D009942:Organometallic Compounds; D014867:Water; D012694:Serine; C072421:isoserine; D012238:Rhodium; C032111:diazoacetic ester