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

被引：35

作者：

Chaume, Gregory ^{[1
]}

Van Severen, Marie-Celine ^{[1
]}

Ricard, Louis ^{[2
]}

Brigaud, Thierry ^{[1
]}

机构：

[1] Univ Cergy Pontoise, CNRS, UMR 8123, Lab Synth Organ Se1ect & Chim Organometall SOS, F-95031 Neuville Sur Oise, Cergy Pontoise, France

[2] Ecole Polytech, CNRS, UMR 7653, Lab Heteroelements & Coordinat, F-91128 Palaiseau, France

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2008年 / 129卷 / 11期

关键词：

alpha-Trifluoromethyl amino acids; Oxazolidines; Organofluorine chemistry; Stereoselective synthesis; Ring closure; Lactams;

D O I：

10.1016/j.jfluchem.2008.07.019

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A straightforward synthesis of enantiopure (S)- and (R)-alpha-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. (c) 2008 Elsevier B.V. All rights reserved.

引用

页码：1104 / 1109

页数：6

共 37 条

[1] COMPARED REACTIVITY OF A BETA-AMINOTHIOL AND A BETA-AMINOALCOHOL TOWARDS PHENYLGLYOXAL [J].