Synthesis, functionalization, and isolation of planar-chiral pillar[5]arenes with bulky substituents using a chiral derivatization agent

Talal F. Al-Azemi; Mickey Vinodh; Fatemeh H. Alipour; Abdirahman A. Mohamod

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Synthesis, functionalization, and isolation of planar-chiral pillar[5]arenes with bulky substituents using a chiral derivatization agent

机译：使用手性衍生剂合成，官能化和分离具有大取代基的平面手性柱[5]芳烃

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Bulky perneopentyloxy-pillar[5]arene ( Pillar-1 ) was synthesized and its conformational mobility was investigated using variable-temperature ~(1) H NMR spectroscopy. The host–guest interactions between Pillar-1 and n -octyltrimethylammonium hexafluorophosphate ( OMA ) were investigated, and the formation of a 1?:?1 complex was revealed via ~(1) H NMR. Planar-chiral isomers were synthesized via the reaction of a hydroxy-functionalized pillar[5]arene with chiral derivatization agent ( S )-(+)-MTPA-Cl. The (Sp, R )-and (Rp, R )-forms of the pillar[5]arene diastereomers were isolated by HPLC, and their structures were analyzed by ~(19) F NMR. HPLC measurements indicated that racemization did not take place at 40 °C for 72 h.

机译：合成了大体积的过戊基戊氧基-立柱[5]芳烃（Pillar-1），并使用可变温度〜（1）H NMR光谱研究了其构象迁移率。研究了Pillar-1和正辛基三甲基铵六氟磷酸酯（OMA）之间的主客体相互作用，并通过〜（1）H NMR揭示了1α：？1络合物的形成。通过羟基官能化的支柱[5]芳烃与手性衍生剂（S）-（+）-MTPA-Cl的反应合成平面手性异构体。柱状[5]芳烃非对映异构体的（Sp，R）-和（Rp，R）-形式通过HPLC分离，并通过〜（19）NMR分析其结构。 HPLC测量表明在40℃下72小时未发生外消旋作用。

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《RSC Advances》 |2019年第40期|共7页
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Talal F. Al-Azemi; Mickey Vinodh; Fatemeh H. Alipour; Abdirahman A. Mohamod;
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1. Synthesis, functionalization, and isolation of planar-chiral pillar[5]arenes with bulky substituents using a chiral derivatization agent [J] . Al-Azemi Talal F., Vinodh Mickey, Alipour Fatemeh H., RSC Advances . 2019,第40期

机译：使用手性衍生化剂，平面 - 手性柱的合成，官能化和平面 - 手性柱[5]的蛋白质蛋白
2. Synthesis, functionalization, and isolation of planar-chiral pillar[5]arenes with bulky substituents using a chiral derivatization agent [J] . Talal F. Al-Azemi, Mickey Vinodh, Fatemeh H. Alipour, RSC Advances . 2019,第40期

机译：使用手性衍生剂合成，官能化和分离具有大取代基的平面手性柱[5]芳烃
3. Planar-chiral macrocyclic host pillar[5]arene: No rotation of units and isolation of enantiomers by introducing bulky substituents [J] . Ogoshi T., Masaki K., Shiga R., Organic letters . 2011,第5期

机译：平面-手性大环主体柱[5]芳烃：通过引入大的取代基而没有单元旋转和对映异构体分离
4. Enantioselective Synthesis of Various Planar-Chiral Metallocenes Catalyzed by Chiral Mo-or Ru-Carbene Complexes [C] . Masamichi Ogasawara, Susumu Watanabe, Kiyohiko Nakajima Symposium on Organometallic Chemistry . 2008

机译：手性Mo-或Ru- Carbene络合催化的各种平面手性茂金属的对映选择性合成
5. Part I. Asymmetric synthesis of bicyclic analogues of risedronate as molecular probes of the mechanism of action of bisphosphonate antiosteoporotic drugs and potentially more efficacious antiosteoporotic agents. Part II. Facile preparation and functionalization of chiral stabilized ylides from common chiral auxiliaries using the Bestmann ylide and their use in Wittig reactions. Part III. Asymmetric organocatalysis: 1. An investigation of alpha-hydroxylation of aldehydes; 2. Synthesis of a novel camphor-based alpha-aminotetrazole organocatalyst. [D] . Song, Xinyi. 2007

机译：第一部分：利塞膦酸盐双环类似物的不对称合成，作为双膦酸盐类抗骨质疏松药和潜在更有效的抗骨质疏松药作用机理的分子探针。第二部分使用Bestmann内酯从常见手性助剂轻松制备和官能化手性稳定化的叶基及其在Wittig反应中的用途。第三部分不对称有机催化：1.醛的α-羟基化研究； 2.合成新的基于樟脑的α-氨基四唑有机催化剂。
6. Synthesis enantioseparation and photophysical properties of planar-chiral pillar5arene derivatives bearing fluorophore fragments [O] . Guojuan Li, Chunying Fan, Guo Cheng, 2019

机译：带有荧光团片段的平面手性柱5芳烃衍生物的合成对映异构和光物理性质
7. Synthesis, functionalization, and isolation of planar-chiral pillar5arenes with bulky substituents using a chiral derivatization agent [O] . Talal F. Al-Azemi, Mickey Vinodh, Fatemeh H. Alipour, 2019

机译：使用手性衍生化剂，平面 - 手性柱的合成，官能化和平面 - 手性柱5的蛋白质蛋白
8. nido-Carborane Building-Block Reagents. 2. Bulky-Substituent (alkyl)2C2B4H6 Derivatives and (C6H5)2C2B4H6: Synthesis and Properties [R] . Boyter, H. A., Grimes, R. N. 1988

机译：nido-Carborane Building-Block Reagents。 2.大体积取代基（烷基）2C2B4H6衍生物和（C6H5）2C2B4H6：合成和性质

Synthesis, functionalization, and isolation of planar-chiral pillar[5]arenes with bulky substituents using a chiral derivatization agent

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