Over last decade, the use of Ni(II) complexes, derived from of glycine Schiff bases with chiral tridentate ligands, has emerge as a leading methodology for preparation of structurally diverse Tailor‐Made Amino Acids, the key structural units in modern medicinal chemistry, and drug design. Here, we report asymmetric synthesis of derivatives of (S)‐α‐(octyl)glycine ((S)‐2‐aminodecanoic acid) and its N‐Fmoc derivative via alkylation of chiral nucleophilic glycine equivalent with n‐octyl bromide. Under the optimized conditions, the alkylation proceeds with excellent yield (98.1%) and diastereoselectivity (98.8% de). The observed stereochemical outcome and convenient reaction conditions bode well for application of this method for large‐scale asymmetric synthesis of (S)‐2‐aminodecanoic acid and its derivatives.

中文翻译：

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通过手性甘氨酸席夫碱的Ni(II)配合物的烷基化不对称合成(S)-α-(辛基)甘氨酸

在过去十年中，使用源自甘氨酸席夫碱和手性三齿配体的 Ni(II) 配合物已成为制备结构多样的定制氨基酸的主要方法，这是现代药物化学中的关键结构单元，和药物设计。这里，我们报告的（衍生物的不对称合成小号）-α-（辛基）甘氨酸（（小号）-2-氨基癸酸）和它的Ñ经由手性亲核甘氨酸当量与烷基化衍生物-Fmoc Ñ-辛基溴。在优化的条件下，烷基化以优异的收率（98.1%）和非对映选择性（98.8% de）进行。观察到的立体化学结果和方便的反应条件预示着该方法可用于大规模不对称合成 ( S )-2-氨基癸酸及其衍生物。