A novel three-component reaction catalyzed by dirhodium(II) acetate: decomposition of phenyldiazoacetate with arylamine and imine for highly diastereoselective synthesis of 1,2-diamines.
[reaction: see text] A practical highly diastereoselective synthesis of 1,2-diamines through carbon-carbon bond formation involving an ammonium ylide intermediate is reported for the first time. By treating methyl phenyldiazoacetate with arylamine and imine in the presence of dirhodium acetate, the erythro diastereomer of methyl 1,2-diaryl-1,2-diaminopropanoate is formed with stereochemical preferences greater than 10:1.
Wang
Yuanhua
Y
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
Zhu
Yanxin
Y
Chen
Zhiyong
Z
Mi
Aiqiao
A
Hu
Wenhao
W
Doyle
Michael P
MP
D000085:Acetates / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003959:Diamines / Q000138:chemical synthesis*; D007097:Imines / Q000737:chemistry*; D008956:Models, Chemical; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D000085:Acetates; D000588:Amines; D003959:Diamines; D007097:Imines; D012238:Rhodium