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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