A Simple Tetraminocalix[4]arene as a Highly Efficient Catalyst under “On-Water” Conditions through Hydrophobic Amplification of Weak Hydrogen Bonds

Margherita De Rosa; Pellegrino La Manna; Annunziata Soriente; Carmine Gaeta; Carmen Talotta; Neal Hickey; Silvano Geremia; Placido Neri

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A Simple Tetraminocalix[4]arene as a Highly Efficient Catalyst under “On-Water” Conditions through Hydrophobic Amplification of Weak Hydrogen Bonds

机译：通过疏水扩增弱氢键的疏水扩增，是一种简单的四氨基碱[4]芳烃作为“水 - 水”条件下的高效催化剂

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The simple tetraminocalix[4]arene 1, which contains weak H-bond-donor NH_2 groups, is reported to be a highly efficient organocatalyst for the Vinylogous Mukaiyama Aldol Reaction (VMAR) of 2-(trimethylsilyloxy)furan 5 with α-ketoesters 6a–l under “on-water” conditions owing to the hydrophobic amplification of weak H-bond interactions. The catalytic efficiency of calixarene catalyst 1 was shown to be closely related to its recognition abilities towards the reactants 5 and 6 through a multipoint recognition model. The proposed model provided good explanations for the differences on the reaction rate acceleration and on the stereoselectivity observed with different substrates.

机译：据报道，含有弱H-BOND-供体NH_2组的简单四氨基碱[4]芳烃1是具有α-酮酯6a的乙烯基富集Mukaiyama Aldol反应（VMAR）的高效有机催化剂，其2-（三甲基甲硅烷基甲硅烷基）呋喃5 - 由于弱H键相互作用的疏水扩增，在“水中”条件下。将钙载催化剂1的催化效率显示在通过多点识别模型中与其朝向反应物5和6的识别能力密切相关。该模型提供了对反应速率加速度的差异以及用不同基材观察到的立体选择性的差异提供了良好的解释。

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来源
《Chemistry: A European journal》 |2017年第29期|共10页
作者
Margherita De Rosa; Pellegrino La Manna; Annunziata Soriente; Carmine Gaeta; Carmen Talotta; Neal Hickey; Silvano Geremia; Placido Neri;
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作者单位

Dipartimento di Chimica e Biologia “A. Zambelli” Università degli Studi di Salerno Via Ponte don Melillo 84084 Fisciano (SA) (Italy) Fax: (+39) 089969603;

Dipartimento di Chimica e Biologia “A. Zambelli” Università degli Studi di Salerno Via Ponte don Melillo 84084 Fisciano (SA) (Italy) Fax: (+39) 089969603;

Dipartimento di Chimica e Biologia “A. Zambelli” Università degli Studi di Salerno Via Ponte don Melillo 84084 Fisciano (SA) (Italy) Fax: (+39) 089969603;

Dipartimento di Chimica e Biologia “A. Zambelli” Università degli Studi di Salerno Via Ponte don Melillo 84084 Fisciano (SA) (Italy) Fax: (+39) 089969603;

Dipartimento di Chimica e Biologia “A. Zambelli” Università degli Studi di Salerno Via Ponte don Melillo 84084 Fisciano (SA) (Italy) Fax: (+39) 089969603;

Centro di Eccellenza in Biocristallografia Dipartimento di Scienze Chimiche e Farmaceutiche Università di Trieste via L. Giorgieri 1 34127 Trieste (Italy);

Centro di Eccellenza in Biocristallografia Dipartimento di Scienze Chimiche e Farmaceutiche Università di Trieste via L. Giorgieri 1 34127 Trieste (Italy);

Dipartimento di Chimica e Biologia “A. Zambelli” Università degli Studi di Salerno Via Ponte don Melillo 84084 Fisciano (SA) (Italy) Fax: (+39) 089969603;

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原文格式 PDF
正文语种 eng
中图分类应用化学;
关键词
aldol reaction; calixarenes; hydrophobic effect; organocatalysts; supramolecular chemistry;

机译：醛醇反应;钙屈剂;疏水效果;有机催化剂;超分子化学;

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1. A Simple Tetraminocalix[4]arene as a Highly Efficient Catalyst under “On-Water” Conditions through Hydrophobic Amplification of Weak Hydrogen Bonds [J] . Margherita De Rosa, Pellegrino La Manna, Annunziata Soriente, Chemistry: A European journal . 2017,第29期

机译：通过疏水扩增弱氢键的疏水扩增，是一种简单的四氨基碱[4]芳烃作为“水 - 水”条件下的高效催化剂
2. Rh-ions and Rh-complexes intercalated in gamma-titanium or gamma-zirconium hydrogen phosphate as highly efficient catalysts for arene hydrogenation [J] . Giannoccaro P, Gargano M, Fanizzi A, Applied Catalysis, A. General: An International Journal Devoted to Catalytic Science and Its Applications . 2005,第1a2期

机译：Rh离子和Rh络合物嵌入γ-钛或γ-锆磷酸氢盐中，作为芳烃加氢的高效催化剂
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机译：Rh离子和Rh络合物嵌入γ-钛或γ-锆磷酸氢盐中，作为芳烃加氢的高效催化剂
4. Ru-catalyzed arene hydrogenation: a highly efficient and selective process for preparing trans-trans isomer of 4,4'-diamino-dicyclohexy [C] . Yuxiang Wang, Dandan Li, Xing Huang, International conference on biotechnology, chemical and materials engineering . 2012

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机译：生物学相关原型中的弱相互作用的高精度计算特征：从三聚体中的氢键结合到蛋白质/配体结合中的pi堆积。
6. Hydrogen-bonding 2D metal-organic solids as highly robust and efficient heterogeneous green catalysts for Biginelli reaction [O] . Peng Li, Sridhar Regati, Raymond J. Butcher, -1

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A Simple Tetraminocalix[4]arene as a Highly Efficient Catalyst under “On-Water” Conditions through Hydrophobic Amplification of Weak Hydrogen Bonds

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