手性柱状芳烃中丙氨酸侧链的平面手性翻转中手性客体分子的关键作用。
Critical Role of Achiral Guest Molecules in Planar Chirality Inversion of Alanine-Appended Pillar[5]arenes.
机构信息
Department of Chemistry and Research Institute of Natural Sciences Gyeongsang National University , Jinju 52828 , Korea.
Accident Prevention and Assessment Division 2 , National Institute of Chemical Safety , Daejeon 34111 , Korea.
出版信息
Org Lett. 2019 Feb 15;21(4):1232-1236. doi: 10.1021/acs.orglett.9b00277. Epub 2019 Feb 7.
Planar chirality inversion of pillar[5]arenes bearing d- or l-alanine substituents on both rims was investigated upon addition of guest molecules having pyridinium or imidazole moieties and long alkyl chains. The d- and l-alanine-substituted pillar[5]arenes exhibited pS and pR planar chirality, respectively. However, this planar chirality was inverted upon inclusion of certain achiral molecules, comprising pyridinium or imidazole moieties and long alkyl chains with terminal hydroxyl or methyl groups.
我们研究了在添加具有吡啶鎓或咪唑部分和长烷基链的客体分子后，带有 d-或 l-丙氨酸取代基的柱[5]芳烃在两个边缘上的平面手性反转。d-和 l-丙氨酸取代的柱[5]芳烃分别表现出 pS 和 pR 平面手性。然而，当包含具有末端羟基或甲基的吡啶鎓或咪唑部分和长烷基链的某些非手性分子时，这种平面手性被反转了。
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