Design of chiral calix arene for synthesis of optically-active unnatural amino acids by asymmetric complexation

不对称络合合成光学活性非天然氨基酸的手性杯芳烃设计

• 批准号: 23750037
• 负责人: TAYAMA Eiji
• 金额: $ 2.91万
• 依托单位: Niigata University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Young Scientists (B)
• 财政年份: 2011
• 资助国家: 日本
• 起止时间: 2011 至 2013
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-23750037/
• 关键词: 不斉包接; 転位反応; 四級アンモニウム塩; アミノ酸; 不斉合成; 有機触媒; 光学活性; 包接; 不斉包接; 転位反応; 四級アンモニウム塩; アミノ酸; 不斉合成; 有機触媒; 光学活性; 包接

Optically-active large cyclic compounds were prepared from calix arenes. NMR analysis of a 1:1 complex between the chiral calix arene and a racemic tetraalkylamkmonium salt was examined. Each enantiomer of the tetraalkylammonium salt were observed separately in the spectrum. Asymmetric rearrangements of the tetraalkylammonium salts using the chiral calix arenes as an organo-catalyst were examined. The rearrangement products were successfully converted to the corresponding unnatural amino acids.

从钙棒制备了光学活跃的大型循环化合物。 对手性钙芳烃与消除甲烷基盐的1：1复合物的NMR分析进行了检查。 在光谱中分别观察到四烷基铵盐的每个对映异构体。 检查了使用手性钙棒作为有机催化剂的四烷基盐盐的不对称重排。 重排产品成功转化为相应的非天然氨基酸。