Enantioselective Diels–Alder reaction in the confined space of homochiral metal–organic frameworks

Tanaka, Kōichi; Nagase, Shohei; Anami, Taku; Wierzbicki, Michał; Urbańczyk‐Lipkowska, Zofia

doi:10.1039/c6ra23740a

Cited by 26 publications

(14 citation statements)

References 40 publications

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“…Synthesis of (R)-CuMOF-1, (R)-CuMOF-2 and (R)-CuMOF-3 (R)-CuMOF-1, 9 (R)-CuMOF-2 10 and (R)-CuMOF-3 11 were synthesized by the methods reported earlier.…”

Section: Resultsmentioning

confidence: 99%

“…9a Recently, we synthesized (R)-CuMOF-2 from (R)-2,2 0 -dihydroxyl-1,1 0 -binaphthalene-4,4 0 -di(4benzoic acid) 2 and its application to the efficient heterogeneous catalyst for the asymmetric Diels-Alder reaction of isoprene with N-ethyl maleimide has been reported. 10 We also constracted (R)-CuMOF-3 from (R)-2,2 0 -dihydroxyl-1,1 0 -binaphthalene-5,5 0 -di(4benzoic acid) 3, which exhibited high catalytic activity in the Diels-Alder reaction of acrolein and 1,3-cyclohexadiene. 11 In this study, we report the synthesis of a novel homochiral (R)-ZnMOF-4 from (R)-2,2 0 -dihydroxy-1,1 0 -binaphthyl-4,4 0 -di(5isophthalic acid) 4 and the application of (R)-CuMOF-1, (R)-CuMOF-2, (R)-CuMOF-3 and (R)-ZnMOF-4 as recyclable heterogeneous catalysts for the ARO reaction of meso-epoxides with some aromatic amines to form optically active b-amino alcohols.…”

Section: Introductionmentioning

confidence: 99%

“…9 a Recently, we synthesized ( R )-CuMOF-2 from ( R )-2,2′-dihydroxyl-1,1′-binaphthalene-4,4′-di(4-benzoic acid) 2 and its application to the efficient heterogeneous catalyst for the asymmetric Diels–Alder reaction of isoprene with N -ethyl maleimide has been reported. 10 We also constracted ( R )-CuMOF-3 from ( R )-2,2′-dihydroxyl-1,1′-binaphthalene-5,5′-di(4-benzoic acid) 3, which exhibited high catalytic activity in the Diels–Alder reaction of acrolein and 1,3-cyclohexadiene. 11 …”

Section: Introductionmentioning

confidence: 99%

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Asymmetric ring-opening reaction of meso-epoxides with aromatic amines using homochiral metal–organic frameworks as recyclable heterogeneous catalysts

et al. 2018

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“…Synthesis of (R)-CuMOF-1, (R)-CuMOF-2 and (R)-CuMOF-3 (R)-CuMOF-1, 9 (R)-CuMOF-2 10 and (R)-CuMOF-3 11 were synthesized by the methods reported earlier.…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Asymmetric ring-opening reaction of meso-epoxides with aromatic amines using homochiral metal–organic frameworks as recyclable heterogeneous catalysts

et al. 2018

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“…Tanaka and co‐workers used chiral organic ligand to prepare chiral MOF and utilized them successfully for enantioselective catalysis . The group has synthesized a series of homochiral ligands and their corresponding homochiral MOF, but the best among them was based on ( R )‐2,2′‐dihydroxy‐1,1′‐ binaphthyl‐4,4′‐dibenzoic acid as the chiral ligand and Cu II as metal centre prepared in a mixed solvent (DMF‐H 2 O) at 55 °C for 4 days.…”

Section: Diels–alder Reactionmentioning

confidence: 99%

Metal‐Organic Frameworks as Platform for Lewis‐Acid‐Catalyzed Organic Transformations

Yadav

Kanoo

2019

Chemistry An Asian Journal

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Metal-organicframeworks (MOFs)are highly promising Lewis acid catalysts;t hey either inherently possess Lewis acid sites (LASs) on it or the LASs can be generated through various post-synthetic methods, the later can be performed in MOFs in at rivial fashion. MOFs are suitable platform for catalysis because of its highly crystalline and porous nature.M oreover,w ith recent advancements, thermal and chemical stability is not ap roblem with many MOFs. In this Minireview, an enormousv ersatility of MOFs,i n terms of their microporosity/mesoporosity,s ize/shapes elec-tivity,c hirality,p ore size, etc.,h as been highlighted. These are advantageous for designing and performing various targeted organic transformations. Although, many organic transformations catalyzed by MOFs with LASs have been reported in the recent past. In this Minireview,w eh ave restricted ourselves to four important organic reactions:(i) cyanosilylation,( ii)Diels-Alder reaction, (iii)C ÀHa ctivation,a nd (iv) CO 2 -addition.T he discussion focuses mostly on the recentr eports (42 examples). Cyanosilylation ReactionCyanosilylation reaction which is nucleophillic addition of trimethylsilylcyanide (TMSCN) to carbonyl compounds producing cyanohydrins is av ery important organic transformation. Cyanohydrins are considered as versatile building blocks for fine chemicals, agrochemicals and pharmaceuticals, that is, a-hydroxyacids, b-hydroxyamines, a-aminonitriles, a-hydroxyketones and b-aminoalcohols. [41][42][43][44] In contrast to other toxic substancess uch as KCN, HCN and NaCN, TMSCN is ap referred reagent for cyanosilylation reactiona si ti se asy to handle, the SiÀCb ond has low dissociation energy andm ost importantly it [a] A.

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“…In 2016, Tanaka et al [93] designed a novel homochiral biphenol-based MOF (29) from the solvothermal reaction of chiral organic ligand (R)-2,2'-dihydroxy-1,1'-binaphthyl-4,4'-dibenzoic acid (H 2 L 15 ) and Cu(NO 3 ) 2 •3H 2 O in a mixed solvent (DMF-H 2 O) at 55 • C for 4 days. The MOF crystallizes in the trigonal space group R32.…”

Section: Diels-alder Reactionmentioning

confidence: 99%

Recent Progress in Asymmetric Catalysis and Chromatographic Separation by Chiral Metal–Organic Frameworks

Bhattacharjee

Khan

et al. 2018

Catalysts

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Metal-organic frameworks (MOFs), as a new class of porous solid materials, have emerged and their study has established itself very quickly into a productive research field. This short review recaps the recent advancement of chiral MOFs. Here, we present simple, well-ordered instances to classify the mode of synthesis of chiral MOFs, and later demonstrate the potential applications of chiral MOFs in heterogeneous asymmetric catalysis and enantioselective separation. The asymmetric catalysis sections are subdivided based on the types of reactions that have been successfully carried out recently by chiral MOFs. In the part on enantioselective separation, we present the potentiality of chiral MOFs as a stationary phase for high-performance liquid chromatography (HPLC) and high-resolution gas chromatography (GC) by considering fruitful examples from current research work. We anticipate that this review will provide interest to researchers to design new homochiral MOFs with even greater complexity and effort to execute their potential functions in several fields, such as asymmetric catalysis, enantiomer separation, and chiral recognition.

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Enantioselective Diels–Alder reaction in the confined space of homochiral metal–organic frameworks

Abstract: A novel homochiral porous MOF synthesized using (R)-2,2′-dihydroxy-1,1′-binaphthyl-4,4′-dibenzoic acid was shown to be an effective heterogeneous catalyst for asymmetric Diels–Alder reaction between isoprene and N-ethyl maleimide.

Cited by 26 publications

References 40 publications

Asymmetric ring-opening reaction of meso-epoxides with aromatic amines using homochiral metal–organic frameworks as recyclable heterogeneous catalysts

Asymmetric ring-opening reaction of meso-epoxides with aromatic amines using homochiral metal–organic frameworks as recyclable heterogeneous catalysts

Metal‐Organic Frameworks as Platform for Lewis‐Acid‐Catalyzed Organic Transformations

Recent Progress in Asymmetric Catalysis and Chromatographic Separation by Chiral Metal–Organic Frameworks

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