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Amino acid ionic liquids as catalysts in a solvent-free Morita-Baylis-Hillman reaction

机译:氨基酸离子液体作为溶剂莫里塔 - 巴利斯 - 山丘反应中的催化剂

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摘要

In the present work, we describe the preparation of ten amino acid ionic liquids (AAILs) formed from ammonium salts as cations, derivatives of glycerol, and natural amino acids as anions. All of them are viscous oils, colorless or pale yellow, and hygroscopic at room temperature. They have appreciable solubility in many protic and aprotic polar solvents. The AAILs were used as catalysts in a Morita-Baylis-Hillman (MBH) reaction. The ionic liquids derivative from l-proline and l-histidine demonstrated the ability to catalyze the reaction between methyl vinyl ketone and aromatic aldehydes differently substituted in the absence of an additional co-catalyst under organic solvent-free conditions. The AAIL derivatives from l-valine, l-leucine, and l-tyrosine catalyzed the MBH reaction only in the presence of imidazole. The MBH adducts were obtained in moderate to good yields. Although the catalytic site in the ILs was in its enantiomerically pure form, all the MBH adducts were obtained in their racemic form.
机译:在本作工作中,我们描述了由铵盐形成的10个氨基酸离子液体(薯类)作为阳离子,甘油的衍生物和天然氨基酸作为阴离子。所有这些都是粘性油,无色或浅黄色,室温下吸湿。它们在许多质粒和非质子极性溶剂中具有明显的溶解性。羊肉用作Morita-Baylis-Hillman(MBH)反应中的催化剂。来自L-脯氨酸和L-组氨酸的离子液体衍生物证明了催化在有机溶剂条件下不存在另外的助催化剂的情况下不同被取代的甲基乙烯基酮和芳族醛之间的反应的能力。来自L-缬氨酸,L-亮氨酸和L-酪氨酸的AAIL衍生物仅在咪唑的存在下催化MBH反应。将MBH加合物中等至良好的产率。虽然ILS中的催化位点处于对映体纯的形式,但所有MBH加合物以其外消旋形式获得。

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  • 来源
    《RSC Advances》 |2018年第42期|共11页
  • 作者单位

    Univ Juiz de Fora Dept Chem Grp Studies Organ Synth &

    Catalysis BR-36036900 Juiz De Fora MG Brazil;

    Univ Juiz de Fora Dept Chem Grp Studies Organ Synth &

    Catalysis BR-36036900 Juiz De Fora MG Brazil;

    Univ Juiz de Fora Dept Chem Grp Studies Organ Synth &

    Catalysis BR-36036900 Juiz De Fora MG Brazil;

    Univ Juiz de Fora Dept Chem Grp Studies Organ Synth &

    Catalysis BR-36036900 Juiz De Fora MG Brazil;

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 化学;
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