Asymmetric Phase-Transfer Catalysts Bearing Multiple Hydrogen-Bonding Donors: Highly Efficient Catalysts for Enantio- and Diastereoselective Nitro-Mannich Reaction of Amidosulfones

Wang, Bin; Liu, Yuxin; Sun, Cong; Wei, Zhonglin; Cao, Jungang; Liang, Dapeng; Lin, Yingjie; Duan, Haifeng

doi:10.1021/ol503264n

Cited by 61 publications

(21 citation statements)

References 49 publications

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“…Two quaternary ammonium compounds (127 and 128), derived from cinchona alkaloids, were synthesized and used as highly efficient catalysts for asymmetric nitro-Mannich reactions of amidosulfones (Scheme 26). When compared to previous reports, a very broad substrate generality was observed, with both enantiomers being achieved with high enantio-and diastereo-selectivity [42].…”

Section: Supramolecular Organocatalysismentioning

confidence: 53%

Organocatalysis: A Brief Overview on Its Evolution and Applications

2018

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The use of small organic molecules as catalysts has gained increasing importance recently. These substances, the so-called organocatalysts, present a lot of advantages, like being less toxic, less polluting, and more economically viable than the organometallic catalysts that dominate asymmetric synthesis. This work intends to briefly show some classic works and recent publications, explaining the advantages of organocatalysis and the different types of compounds used in this field, as well as their course of action.

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Section: Supramolecular Organocatalysismentioning

confidence: 53%

Organocatalysis: A Brief Overview on Its Evolution and Applications

2018

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“…However, over the last five years, several groups have started to systematically investigate the introduction of alternative H‐bonding donors, i.e. ureas and thioureas to obtain new classes of highly active bifunctional ammonium salt catalysts [66–75] . Chiral back‐bones were derived from the natural chiral pool like Cinchona alkaloids; [66–70] amino acids; [71–73] or from easily available chiral diamines, i.e.…”

Section: Introductionmentioning

confidence: 99%

“…ureas and thioureas to obtain new classes of highly active bifunctional ammonium salt catalysts. [ 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 74 , 75 ] Chiral back‐bones were derived from the natural chiral pool like Cinchona alkaloids;[ 66 , 67 , 68 , 69 , 70 ] amino acids;[ 71 , 72 , 73 ] or from easily available chiral diamines, i.e. trans ‐cyclohexane diamine.…”

Section: Introductionmentioning

confidence: 99%

Study of Ground State Interactions of Enantiopure Chiral Quaternary Ammonium Salts and Amides, Nitroalkanes, Nitroalkenes, Esters, Heterocycles, Ketones and Fluoroamides

Bencivenni¹,

Illera²,

Moccia

et al. 2021

Chemistry A European J

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Chiral phase‐transfer catalysis provides high level of enantiocontrol, however no experimental data showed the interaction of catalysts and substrates. 1H NMR titration was carried out on Cinchona and Maruoka ammonium bromides vs. nitro, carbonyl, heterocycles, and N−F containing compounds. It was found that neutral organic species and quaternary ammonium salts interacted via an ensemble of catalyst +N−C−H and (sp2)C−H, specific for each substrate studied. The correspondent BArF salts interacted with carbonyls via a diverse set of +N−C−H and (sp2)C−H compared to bromides. This data suggests that BArF ammonium salts may display a different enantioselectivity profile. Although not providing quantitative data for the affinity constants, the data reported proofs that chiral ammonium salts coordinate with substrates, prior to transition state, through specific C−H positions in their structures, providing a new rational to rationalize the origin of enantioselectivity in their catalyses.

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“…In 2014, Duan's group firstly introduced multiple hydrogen bonds into the chiral PTC derived from cinchona alkaloids, as shown in Scheme 8 [24]. The new family of bifunctional catalysts have been successfully applied to the nitro-Minnich reactions with a broad substrate scope.…”

Section: Scheme 6 Asymmetric Henry Reactions Of Ketoiminesmentioning

confidence: 99%

Chiral Phase-Transfer Catalysts with Hydrogen Bond: A Powerful Tool in the Asymmetric Synthesis

Wang

2019

Catalysts

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Asymmetric phase-transfer catalysis has been widely applied into organic synthesis for efficiently creating chiral functional molecules. In the past decades, chiral phase-transfer catalysts with proton donating groups are emerging as an extremely significant strategy in the design of novel catalysts, and a large number of enantioselective reactions have been developed. In particular, the proton donating groups including phenol, amide, and (thio)-urea exhibited unique properties for cooperating with the phase-transfer catalysts, and great advances on this field have been made in the past few years. This review summarizes the seminal works on the design, synthesis, and applications of chiral phase-transfer catalysts with strong hydrogen bonding interactions.

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Asymmetric Phase-Transfer Catalysts Bearing Multiple Hydrogen-Bonding Donors: Highly Efficient Catalysts for Enantio- and Diastereoselective Nitro-Mannich Reaction of Amidosulfones

Cited by 61 publications

References 49 publications

Organocatalysis: A Brief Overview on Its Evolution and Applications

Organocatalysis: A Brief Overview on Its Evolution and Applications

Study of Ground State Interactions of Enantiopure Chiral Quaternary Ammonium Salts and Amides, Nitroalkanes, Nitroalkenes, Esters, Heterocycles, Ketones and Fluoroamides

Chiral Phase-Transfer Catalysts with Hydrogen Bond: A Powerful Tool in the Asymmetric Synthesis

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