Prev. Article Next Article Table of Contents

Note

Synthesis of Hydantoins from Enantiomerically Pure α-Amino Amides without Epimerization

Supporting Info

Dun Zhang,^† Xuechao Xing,^‡ and Gregory D. Cuny*^‡

Department of Chemical & Biological Engineering, Tufts University, Science and Technology Center, 4 Colby Street, Medford, Massachusetts 02155, and Laboratory for Drug Discovery in Neurodegeneration, Brigham & Women's Hospital and Harvard Medical School, 65 Landsdowne Street, Cambridge, Massachusetts 02139 gcuny@rics.bwh.harvard.edu

J. Org. Chem., 2006, 71 (4), pp 1750–1753

DOI: 10.1021/jo052474s

Publication Date (Web): January 27, 2006

†

Tufts University.

‡

Brigham & Women's Hospital and Harvard Medical School.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

A method for the preparation of enantiomerically pure hydantoins from optically pure α-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.

View: Full Text HTML | Hi-Res PDF