Enantioselective Chromatographic Resolution and One-Pot Synthesis of Enantiomerically Pure Sulfoxides over a Homochiral Zn−Organic Framework

Nuzhdin, Alexey L.; Dybtsev, Danil N.; Bryliakov, Konstantin P.; Talsi, Evgenii P.; Fedin, Vladimir P.

doi:10.1021/ja076276p

Cited by 254 publications

(155 citation statements)

References 16 publications

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“…Although the authors could recycle the catalyst for 30 catalytic cycles, they failed to observe any asymmetric induction in the catalytic sulfoxidation. In a later report this MOF was applied at the same time as a catalyst and as a chiral stationary phase for a column to obtain enantiomerically pure sulfoxides 130 . However, the enantioseparation of the bulkier sulfoxides could not be obtained due to the relative small pore dimensions of the MOF.…”

Section: Mofs In Chiral Oxidation Catalysismentioning

confidence: 99%

Metal-Organic Frameworks as Selective or Chiral Oxidation Catalysts

2014

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Since the discovery of Metal Organic Frameworks (MOFs) in the early 1990, the amount of new structures has grown exponentially. A MOF typically consists of inorganic nodes that are connected by organic linkers to form crystalline, highly porous structures. MOFs have attracted a lot of attention lately, as the versatile design of such materials holds promises of interesting applications in various fields. In this review, we will focus on the use of MOFs as heterogeneous oxidation catalysts. MOFs are very promising candidates to replace homogeneous catalysts by sustainable and stable heterogeneous catalysts. The catalytic active function can be either the active metal sites of the MOF itself or can be introduced as an extra functionality in the linker, a dopant or a "ship-in-a-bottle" complex. As the pore size, pore shape and functionality of MOFs can be designed in numerous ways, shape selectivity and even chiral selectivity can be created. In this review, we will present an overview on the state of the art of the use of MOFs as a heterogeneous catalyst in liquid phase oxidation reactions.

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Section: Mofs In Chiral Oxidation Catalysismentioning

confidence: 99%

Metal-Organic Frameworks as Selective or Chiral Oxidation Catalysts

2014

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“…Chiral MOF catalysts with uniform active sites for enantioselective reactions have been developed based on functionalized chiral molecular (pre)catalysts [21][22][23][24][25][26][27][28][29][30] . In a handful of latest studies, the resolution of enantiomers (racemic alcohols and sulphoxides) with chiral MOFs via chromatography [31][32][33][34] , crystallization [35][36][37][38][39][40] and membrane 41,42 has been reported, but only few exhibit good chiral separation performance.…”

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confidence: 99%

Engineering chiral porous metal-organic frameworks for enantioselective adsorption and separation

et al. 2014

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The separation of racemic molecules is of substantial significance not only for basic science but also for technical applications, such as fine chemicals and drug development. Here we report two isostructural chiral metal-organic frameworks decorated with chiral dihydroxy or -methoxy auxiliares from enantiopure tetracarboxylate-bridging ligands of 1,1 0 -biphenol and a manganese carboxylate chain. The framework bearing dihydroxy groups functions as a solid-state host capable of adsorbing and separating mixtures of a range of chiral aromatic and aliphatic amines, with high enantioselectivity. The host material can be readily recycled and reused without any apparent loss of performance. The utility of the present adsorption separation is demonstrated in the large-scale resolution of racemic 1-phenylethylamine. Control experiments and molecular simulations suggest that the chiral recognition and separation are attributed to the different orientations and specific binding energies of the enantiomers in the microenvironment of the framework.

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“…Furthermore, the pore surfaces of porous MOFs can be functionalized by the immobilization of different recognition sites, such as open metal sites, Lewis basic/acidic sites and chiral pockets, to direct the recognition of small molecules [6][7][8][9][10][11][12][13][14] . Systematically tuning micropores can achieve size-specific encapsulation of small gas molecules, and immobilization of functional sites enables varying substrate interactions: microporous MOF materials have emerged as promising microporous media for the recognition and separation of small molecules [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32] . Kitagawa pioneered the research on construction of porous mixed-metal-organic frameworks (M′MOFs) by making use of MSalen metalloligands in 2004 (refs 15, 16).…”

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confidence: 99%

Rationally tuned micropores within enantiopure metal-organic frameworks for highly selective separation of acetylene and ethylene

et al. 2011

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separation of acetylene and ethylene is an important industrial process because both compounds are essential reagents for a range of chemical products and materials. Current separation approaches include the partial hydrogenation of acetylene into ethylene over a supported Pd catalyst, and the extraction of cracked olefins using an organic solvent; both routes are costly and energy consuming. Adsorption technologies may allow separation, but microporous materials exhibiting highly selective adsorption of C 2 H 2 /C 2 H 4 have not been realized to date. Here, we report the development of tunable microporous enantiopure mixed-

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Enantioselective Chromatographic Resolution and One-Pot Synthesis of Enantiomerically Pure Sulfoxides over a Homochiral Zn−Organic Framework

Cited by 254 publications

References 16 publications

Metal-Organic Frameworks as Selective or Chiral Oxidation Catalysts

Metal-Organic Frameworks as Selective or Chiral Oxidation Catalysts

Engineering chiral porous metal-organic frameworks for enantioselective adsorption and separation

Rationally tuned micropores within enantiopure metal-organic frameworks for highly selective separation of acetylene and ethylene

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