Concise access to enantiopure (S)- and (R)-α-trifluoromethyl pyroglutamic acids from ethyl trifluoropyruvate-based chiral CF3-oxazolidines (Fox)

A straightforward synthesis of enantiopure (S)- and (R)-α-Tfm-pyroglutamic acid is reported. The strategy is based on the use of a chiral CF3-hydroxymorpholinone intermediate conveniently obtained from ethyl trifluoropyruvate-based chiral CF3-oxazolidines (Fox). The key step is an oxidative cyclization followed by a reductive cleavage of the (R)-phenylglycinol chiral auxiliary.

Graphical abstractA straightforward synthesis of enantiopure (S)- and (R)-α-Tfm-pyroglutamic acid ethyl trifluoropyruvate-based chiral CF3-oxazolidines (Fox) is reported.Figure optionsDownload full-size imageDownload as PowerPoint slide