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  • Synthesis of hydantoins from enantiomerically pure alpha-amino amides without epimerization.

Synthesis of hydantoins from enantiomerically pure alpha-amino amides without epimerization.

The Journal of organic chemistry (2006-02-14)
Dun Zhang, Xuechao Xing, Gregory D Cuny
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Bis(trichloromethyl) carbonate, purum, ≥99.0% (AT)
Sigma-Aldrich
Triphosgene, reagent grade, 98%