Chiral Metal–Organic Frameworks Bearing Free Carboxylic Acids for Organocatalyst Encapsulation

Liu, Yan; Xi, Xiaobing; Ye, Chengcheng; Gong, Tengfei; Yang, Zhiwei; Cui, Yong

doi:10.1002/ange.201408896

Cited by 21 publications

(4 citation statements)

References 61 publications

(10 reference statements)

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“…Direct Method: Using chiral ligands as initial reactants to synthesize CMOFs is currently the most widely used, simplest, and most effective method. [179] The direct method for the synthesis of chiral metal-organic frameworks is shown in Figure 11. Some common chiral small molecules, such as tartaric acid, camphoric acid, natural amino acids, etc., are relatively cheap and readily available.…”

Section: Synthetic Chiral Coordination Structurementioning

confidence: 99%

Chiral Materials: Progress, Applications, and Prospects

Niu

Zhao

Yan

et al. 2023

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Chirality is a universal phenomenon in molecular and biological systems, denoting an asymmetric configurational property where an object cannot be superimposed onto its mirror image by any kind of translation or rotation, which is ubiquitous on the scale from neutrinos to spiral galaxies. Chirality plays a very important role in the life system. Many biological molecules in the life body show chirality, such as the “codebook” of the earth's biological diversity‐DNA, nucleic acid, etc. Intriguingly, living organisms hierarchically consist of homochiral building blocks, for example, l‐amino acids and d‐sugars with unknown reason. When molecules with chirality interact with these chiral factors, only one conformation favors the positive development of life, that is, the chiral host environment can only selectively interact with chiral molecules of one of the conformations. The differences in chiral interactions are often manifested by chiral recognition, mutual matching, and interactions with chiral molecules, which means that the stereoselectivity of chiral molecules can produce changes in pharmacodynamics and pathology. Here, the latest investigations are summarized including the construction and applications of chiral materials based on natural small molecules as chiral source, natural biomacromolecules as chiral sources, and the material synthesized by design as a chiral source.

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Section: Synthetic Chiral Coordination Structurementioning

confidence: 99%

Chiral Materials: Progress, Applications, and Prospects

Niu

Zhao

Yan

et al. 2023

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“…However, the corresponding MOF obtained by mixing the chiral moiety has shown lower enantioselectivity. Two chiral porous MOFs functionalized with carboxylic acid groups were reported for the first time by Liu et al [136]. One of them was able to encapsulate S)-2-(dimethylaminomethyl) pyrrolidine by combining the carboxylic acids and chiral amines in situ through acid-base interactions.…”

Section: Some Examples Of Heterogeneous Organocatalysts In Solvent-free Conditionsmentioning

confidence: 99%

Recent Advances in Sustainable Organocatalysis

Branco¹,

Phillips²,

Marques³

et al. 2016

Recent Advances in Organocatalysis

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The recent advances on green and sustainable organocatalysis are revised in this chapter. An important focus on one of the 12 principles of green chemistry, organocatalysis pursues to reduce energy consumption as well as to optimize the use of different resources, targeting to become a sustainable strategy in organic chemical transformations. In last decades, several experimental methodologies have been performed to make organocatalysis an even greener and sustainable alternative to stoichiometric approaches as well as non-catalytic conditions by the use of benign and friendlier reaction media. In this line, several approaches using water as preferential solvent, alternative solvents such as ionic liquids including chiral ones, deep eutectic solvents, polyethylene glycol (PEG), supercritical fluids and organic carbonates or solvent-free methodologies have been reported. In this chapter, we mainly focus on the recent remarkable advancements in organocatalysis using green and sustainable protocols.

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“…Among the applications, immobilization of homogeneous catalysts, especially chiral catalysts, on cavity surfaces of the solid porous materials is of great importance. In this field, the latest developments involved enantioselective catalysis based on metal-organic frameworks (MOFs) [1][2][3][4][5][6][7][8][9][10][11][12][13][14], covalent organic frameworks (COFs) [15][16][17][18][19][20][21][22][23][24] and porous organic polymers (POPs) [25][26][27][28][29][30][31][32]. Many advantages of MOFs, COFs and POPs for heterogeneous enantioselective catalysis have been elaborated by scientists.…”

Section: Introductionmentioning

confidence: 99%

“…Meanwhile, owing to the appropriate size as well as the easy preparation, the proline-type organocatalysts are one of the best candidates to investigate if a new solid material could be used as the platform for enantioselective catalysis. On the other hand, the Aldol reaction is an important reaction which is frequentlyused to investigate the catalytic activity of the catalyst supported by porous materials such as MOFs, COFs and POPs [1][2][3][4][5][6][7][8][9]23,24,32]. Thus in this paper we make an attempt to introduce the chiral catalytically active L-prolinamide unit into the PAF-1 material by stepwise post-synthetic modifications and investigate the catalytic performance of the obtained material for catalyzing the Aldol reaction.…”

Section: Introductionmentioning

confidence: 99%

Porous aromatic framework (PAF-1) as hyperstable platform for enantioselective organocatalysis

et al. 2018

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High density of phenyl rings makes PAF-1 have robust structure and highly lipophilic pore, which make it very suitable for organocatalysis. However, there is no report about using PAF-1 as platform for enantioselective organocatalysis. In this paper, using PAF-1 as the platform, a chiral prolinamide catalytic site was introduced onto the framework of PAF-1 via a series of stepwise post-synthetic modifications, obtaining a novel PAF-supported chiral catalyst named PAF-1-NHPro. Then its enantioselective catalytic performance was studied by subjecting it to catalyze the model Aldol reaction between p-nitrobenzaldehyde and cyclohexanone. PAF-1-NHPro showed good diastereoselectivity and enantioselectivity with excellent and easy recyclability.

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Chiral Metal–Organic Frameworks Bearing Free Carboxylic Acids for Organocatalyst Encapsulation

Cited by 21 publications

References 61 publications

Chiral Materials: Progress, Applications, and Prospects

Chiral Materials: Progress, Applications, and Prospects

Recent Advances in Sustainable Organocatalysis

Porous aromatic framework (PAF-1) as hyperstable platform for enantioselective organocatalysis

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