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4, and filtered, and the solvent was removed in vacuo affording the wanted amides after flash column chromatography purification (hexanes:AcOEt 2:8). All amides gave physical and spectroscopic data consistent with the proposed structures.
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13C NMR resonance for the C=N group indicating that only one of the two possible E/Z isomers of the azomethyne bond was present. The preference for the E configuration in imines in which the C=N bond is conjugated with one or more aromatic rings has already been described. Hine, J.; Yeh, C. Y. J. Am. Chem. Soc. 1967, 89, 2669.
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4 and filtered, and the solvent was removed in vacuo, affording the desired β-aminoesters after flash column chromatography purification (hexanes:AcOEt 1:1). All products gave physical and spectroscopic data consistent with the proposed structures.
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1H NMR spectrum of the reaction crude showed the presence of only one diastereoisomer with respect to the relative configuration between both chiral centers. HPLC analysis under conditions optimized for racemic (±)-5a (ChiralcelOD, UV detector, n-hexane/2-propanol 95:5, 0.80 mL/min) indicated the presence of only one of the two possible ones.
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