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

Dun Zhang; Xuechao Xing; Gregory D Cuny

doi:10.1021/jo052474s

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

J Org Chem. 2006 Feb 17;71(4):1750-3. doi: 10.1021/jo052474s.

Authors

Dun Zhang¹, Xuechao Xing, Gregory D Cuny

Affiliation

¹ Department of Chemical & Biological Engineering, Tufts University, Science and Technology Center, 4 Colby Street, Medford, Massachusetts 02155, USA.

PMID: 16468841
DOI: 10.1021/jo052474s

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amides / chemistry*
Hydantoins / chemical synthesis*
Imidazoles
Phosgene / analogs & derivatives
Stereoisomerism

Substances

Amides
Hydantoins
Imidazoles
Phosgene
bis(trichloromethyl) carbonate
imidazole