Stereochemistry of direct conversion of polyamides to hydroxyesters was investigated using model compounds. Optically active secondary-alkyl amines underwent the conversion to corresponding secondary alcohols in moderate yields by treatment with supercritical methanol in the presence of glycolic acid. The reaction progressed through almost completely stereochemical inversion to give secondary alcohols in high yields. Thus, the substitution reaction of the amino group to hydroxyl group progresses through S_N2 type transition state accompanying with stereoinversion.

中文翻译：

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以单体仲手性胺为模型化合物的聚酰胺直接转化为羟基酯的立体化学研究

使用模型化合物研究了聚酰胺直接转化为羟基酯的立体化学。通过在乙醇酸存在下用超临界甲醇处理，光学活性仲烷基胺以中等收率转化成相应的仲醇。反应通过几乎完全立体化学转化进行，以高收率得到仲醇。因此，氨基与羟基的取代反应通过伴随立体反转的S _N 2型转变状态进行。