We describe here an asymmetric aldol reaction based on the principle of Memory of Chirality. From α-amino acids such as leucine and methionine, we have synthesized in two steps quaternary α-amino acid derivatives with high diastereoselectivity and enantioselectivity, using the chirality of the initial α-amino acid as the only chirality source. Furthermore, we were able to determine the relative and absolute configurations of the aldol products thanks to crystallographic structures and thus showed that the relative configuration depended on the aldehyde employed. We proposed a stereoselectivity explanation and obtained also quaternary β-hydroxy α-amino acids after acidic hydrolysis.

中文翻译：

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手性记忆的高立体选择性羟醛反应：季 β-羟基 α-氨基酸的合成

我们在这里描述了基于手性记忆原理的不对称醛醇反应。从α-氨基酸如亮氨酸和甲硫氨酸，我们以初始α-氨基酸的手性作为唯一的手性来源，分两步合成了具有高非对映选择性和对映选择性的季α-氨基酸衍生物。此外，由于晶体结构，我们能够确定醛醇产物的相对和绝对构型，因此表明相对构型取决于所使用的醛。我们提出了立体选择性解释，并在酸性水解后获得了季 β-羟基 α-氨基酸。