Diastereoselective cycloaddition of (S)-N-(1-phenylethylimino) trifluoropropionate and trifluoroethylphosphonate with diazomethane

作者：Rassukana Yuliya V; Bezgubenko Ludmyla V; Stanko Oleg V; Rusanov Eduard B; Kulik Irina B; Onys'ko Petro P^*

来源：Tetrahedron: Asymmetry , 2017, 28(4): 555-560.

DOI：10.1016/j.tetasy.2017.03.009

The cycloaddition reaction of (S)-(alpha-phenylethylimino)trifluoropropionate with diazomethane leads to a diastereomeric mixture (4.5:1) of 5-trifluoromethyl-1,2,3-triazoline-5-carboxylates. Enantiopure diastereomers were isolated by column chromatography and converted into their respective non-racemic 2-trifluoromethyl-aziridine-2-carboxylates and carboxylic acids. The absolute configuration of newly formed stereogenic centers was determined by XRD analysis. The stereoselective reaction between (S)N-(alpha-phenylethyl)trifluoroacetimidoylphosphonate and diazomethane produces a diastereomeric mixture (2.5:1) of 5-trifluoromethyltriazoline-5-phosphonates readily separated by column chromatography in diastereomerically pure forms.

• 出版日期2017-4-15