Lensen Nathalie, Marais Joyce, Brigaud Thierry
Laboratoire de Chimie Biologique (LCB), EA 4505, Université de Cergy-Pontoise , 5 Mail, Gay-Lussac, Neuville sur Oise, 95000 Cergy-Pontoise Cedex, France.
Org Lett. 2015 Jan 16;17(2):342-5. doi: 10.1021/ol503448w. Epub 2015 Jan 6.
The straightforward syntheses of enantiopure (2R)-2-trifluoromethyl-2-carboxyazetidine and (R)- and (S)-trifluoromethylhomoserines are reported. The key step is a Strecker-type reaction on a common chiral CF3-containing bicyclic oxazolidine intermediate obtained by a condensation reaction of (R)-phenylglycinol and ethyl-4,4,4-trifluoroacetoacetate (ETFAA).
报道了对映体纯的(2R)-2-三氟甲基-2-羧基氮杂环丁烷以及(R)-和(S)-三氟甲基高丝氨酸的直接合成方法。关键步骤是在由(R)-苯基甘氨醇与4,4,4-三氟乙酰乙酸乙酯(ETFAA)缩合反应得到的常见含手性CF3的双环恶唑烷中间体上进行Strecker型反应。