Enantioselective trapping of phosphoramidate ammonium ylides with imino esters for synthesis of 2,3-diaminosuccinic acid derivatives.
A highly enantioselective trapping of protic phosphoramidate ammonium ylides with α-imino esters is reported. The intriguing Rh2(OAc)4 and chiral Brønsted acid co-catalyzed three-component Mannich-type reaction of a diazo compound, a phosphoramidate, and an α-imino ester provides a rapid and efficient access to 2,3-diaminosuccinic acid derivatives with a high level control of diastereo- and enantioselectivity.
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, 3663 North Zhongshan Rd., Shanghai, 200062, China.
Jun
J
Jiang
Xiaochu
X
Ma
Shunying
S
Liu
Yu
Y
Qian
Fengping
F
Lv
Lin
L
Qiu
Xiang
X
Wu
Wenhao
W
Hu
D000577:Amides / Q000737:chemistry*; D000599:Amino Acids, Diamino / Q000138:chemical synthesis / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry; D018360:Crystallography, X-Ray; D004952:Esters; D007097:Imines / Q000737:chemistry*; D008968:Molecular Conformation; D010756:Phosphoric Acids / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
D000577:Amides; D000599:Amino Acids, Diamino; D001391:Azo Compounds; D056831:Coordination Complexes; D004952:Esters; D007097:Imines; D010756:Phosphoric Acids; D000644:Quaternary Ammonium Compounds; C031934:diaminosuccinic acid; C011067:phosphoramidic acid; D012238:Rhodium