Synthesis and structures of three new pyridine-containing oxazoline ligands of complexes for asymmetric catalysis,Acta Crystallographica Section C

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Synthesis and structures of three new pyridine-containing oxazoline ligands of complexes for asymmetric catalysis
Acta Crystallographica Section C ( IF 0.7 ) Pub Date : 2021-08-18 , DOI: 10.1107/s2053229621008202
Ewa Wolińska ₁ , Waldemar Wysocki ₁ , Danuta Branowska ₁ , Zbigniew Karczmarzyk ₁

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Three new chiral pyridine-containing oxazoline derivatives with fluorine and perfluoromethyl groups, namely, 2-({2-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl}amino)-5-(trifluoromethyl)pyridine, C₂₁H₁₆F₃N₃O, 2-({5-fluoro-2-[(4S)-4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl}amino)-5-(trifluoromethyl)pyridine, C₁₈H₁₇F₄N₃O, and 2-({2-[(3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl]phenyl}amino)-5-(trifluoromethyl)pyridine, C₂₂H₁₆F₃N₃O, as chiral ligands in metal-catalysed asymmetric reactions, were synthesized and characterized by spectral and X-ray diffraction methods. The conformation of the molecules is influenced by strong N—H…N hydrogen bonding and weak C—H…X (X = O and N) interactions. There are no intermolecular hydrogen bonds in the crystal structures of the analysed compounds. Hirshfeld surface analysis showed that the H…H contacts constitute a high percentage of the intermolecular interactions. The conformational analysis was performed by theoretical calculations using the density functional theory (DFT) method. The mechanism of complex formation in terms of the electron-withdrawing effect of the substituents on the oxazoline ring and the ligand conformation is discussed.

中文翻译：

不对称催化配合物的三种新型含吡啶恶唑啉配体的合成与结构

三种新的含氟和全氟甲基的手性含吡啶恶唑啉衍生物，即2-({2-[(4 S )-4-苯基-4,5-二氢-1,3-恶唑-2-基]苯基}氨基)-5-(三氟甲基)吡啶，C ₂₁ H ₁₆ F ₃ N ₃ O，2-({5-氟-2-[(4 S )-4-异丙基-4,5-二氢-1,3-恶唑-2-基]苯基}氨基)-5-(三氟甲基)吡啶、C ₁₈ H ₁₇ F ₄ N ₃ O和2-({2-[(3a R ,8a S )-8,8a-二氢- 3a H-茚并[1,2 - d ]恶唑-2-基]苯基}氨基)-5-(三氟甲基)吡啶，C ₂₂ H ₁₆F ₃ N ₃ O 作为金属催化不对称反应中的手性配体被合成并通过光谱和X 射线衍射方法表征。分子的构象受强 N—H…N 氢键和弱 C—H… X ( X = O 和 N) 相互作用。被分析化合物的晶体结构中没有分子间氢键。Hirshfeld 表面分析表明 H…H 接触构成分子间相互作用的高百分比。使用密度泛函理论 (DFT) 方法通过理论计算进行构象分析。从取代基对恶唑啉环和配体构象的吸电子作用的角度讨论了配合物形成的机制。

更新日期：2021-09-06

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