Synthesis of Hydantoins from Enantiomerically Pure α-Amino Amides without Epimerization
Dun Zhang, Xuechao Xing and Gregory D. Cuny*
*Laboratory for Drug Discovery in Neurodegeneration, Brigham & Women's Hospital and Harvard Medical School, 65 Landsdowne Street, Cambridge, Massachusetts 02139, Email: gcunyrics.bwh.harvard.edu
D. Zhang, X. Xing, G. D. Cuny, J. Org. Chem., 2006, 71, 1750-1753.
DOI: 10.1021/jo052474s (free Supporting Information)
Enantiomerically pure hydantoins are prepared from optically pure α-amino amides utilizing triphosgene. A mechanism for the racemization observed with 1,1'-carbonyldiimidazole (CDI) for this type of reaction is proposed.
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