Straightforward synthesis of (S)- and (R)-α-trifluoromethyl proline from chiral oxazolidines derived from ethyl trifluoropyruvate

被引：89

作者：

Chaume, Gregory ^{[1
]}

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

Marinkovic, Sinisa ^{[1
]}

Brigaud, Thierry ^{[1
]}

机构：

[1] Univ Cergy Pontoise, CNRS, UMR 8123, Lab Synth Organ Select & Chim Organomet,SOSCO, F-95031 Neuville Sur Oise, Cergy Pontoise, France

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 26期

关键词：

D O I：

10.1021/ol062593+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise synthesis of both enantiomers of alpha-Tfm-proline and (S)-alpha-Tfm-prolinol from ethyl trifluoropyruvate is reported. The key step is a diastereoselective allylation reaction of ethyl trifluoropyruvate and (R)-phenylglycinol-based oxazolidines or imine. The lactone obtained by cyclization of the resulting hydroxy ester proved to be a valuable intermediate for the synthesis of (S)-alpha-Tfm-allylglycine and (S)-alpha-Tfm-norvaline in enantiopure form.

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页码：6123 / 6126

页数：4

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