An asymmetric synthesis ofl-[2-13C]aspartic acid from sodium [2-13C]acetate

Abstract

l-[2-13C]Aspartic acid was synthesized by using Dellaria's oxazinone labelled with 13C at the 3-position, prepared from phenyl [2-13C]bromoacetate and (S)-2-phenylglycinol, as a chiral glycine equivalent. Phenyl [2-13C]bromoacetate was derived from sodium [2-13C]acetate. Alkylation of the [3-13C]oxazinone with ethyl bromoacetate was achieved with high diastereoselectivity. Finally, sequential deprotection and removal of the chiral auxiliary of the alkylated [3-13C]oxazinone afforded l–[2-13C]aspartic acid. Copyright © 1999 John Wiley & Sons, Ltd.