Abstract
The cycloaddition reaction of (S)-(α-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-(α-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.
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