Synthesis of hydantoins from enantiomerically pure alpha-amino amides without epimerization.
A method for the preparation of enantiomerically pure hydantoins from optically pure alpha-amino amides utilizing triphosgene is described. We also propose that the racemization observed with 1,1'-carbonyldiimidazole (CDI) for this type of reaction is due to the imidazole carbamate intermediates.
Department of Chemical & Biological Engineering, Tufts University, Science and Technology Center, 4 Colby Street, Medford, Massachusetts 02155, USA.
Dun
D
Zhang
Xuechao
X
Xing
Gregory D
GD
Cuny
D000577:Amides / Q000737:chemistry*; D006827:Hydantoins / Q000138:chemical synthesis*; D007093:Imidazoles; D010705:Phosgene / Q000031:analogs & derivatives; D013237:Stereoisomerism
D000577:Amides; D006827:Hydantoins; D007093:Imidazoles; D010705:Phosgene; C111044:bis(trichloromethyl) carbonate; C029899:imidazole