1,4-苯并硫烷,2-或3-取代,是一个重要的脚手架,尽管它存在于几种治疗剂中,它是化学未开发的。此外,文献中只有少数实例报道了该部分的对映体纯形式。这里,利用(S)-苯乙胺形成非对映体酰胺,在1H-核磁共振(NMR)光谱和其他物理化学性质方面显示显着差异,我们首次定义了每种酰胺的绝对构型,2-或3-取代。此外,非对映体酰胺在酸性条件下进一步水解,让实现相应的1,4-苯并恶杂羧酸。
1,4-Benzoxathiane, 2- or 3-substituted, is an important scaffold, and despite its presence in several therapeutic agents, it is chemically unexploited. Furthermore, only a few examples in literature report this moiety in its enantiopure form. Here, taking advantage to the formation of diastereomeric amides by using (S)-phenylethylamine, which show significant differences in terms of 1 H-nuclear magnetic resonance (NMR) spectra and other physical chemical properties, we defined for the first time the absolute configuration of each amide, both 2- or 3-substituted. Moreover, the diastereomeric amides were further hydrolyzed in acid conditions, letting to the achievement of the corresponding 1,4-benzoxathian carboxylic acids.