Enantioselective Catalytic Reactions with <i>N</i>-Acyliden Penta-atomic Aza-heterocycles. Heterocycles as Masked Bricks To Build Chiral Scaffolds

Desimoni, G.; Faita, Giuseppe; Quadrelli, Paolo

doi:10.1021/acs.chemrev.5b00097

Cited by 59 publications

(22 citation statements)

References 139 publications

(446 reference statements)

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“…On the other hand, the rate of the subsequent lactonisation step correlates with the heterocycle leaving group ability, which could be roughly evaluated considering the heterocyclic anion stability and so the p Ka values of the conjugate acid [5b] . Indeed, the yield of product 3 was found to increase from moderate to high when moving from acceptors containing pyrrole or imidazole to those bearing benzotriazole and triazole groups (Scheme 4).…”

Section: Pyrazoleamides As Electrophiles In Organocatalysismentioning

confidence: 99%

Pyrazoleamides in Catalytic Asymmetric Reactions: Recent Advances

et al. 2021

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Pyrazoleamides are a class of compounds which have received significant attention in the last years in asymmetric catalysis as more reactive and practical surrogates of esters or amides. These readily available reagents have served in a variety of diastereo-and enantioselective metal-and organocatalytic transformations, spanning from simple carbon-carbon or carbon-heteroatom bond formation to cascade and rearrangement reactions, to produce valuable classes of heterocyclic compounds. More recently, pyrazoleamides have proved to be pertinent reagents in asymmetric catalysis merged with photoredox catalysis, and in more challenging stereoselective bond-forming reactions, occurring directly from a visible-light activated substrate/catalyst complex without any charge separation. Both strategies enable new activation concepts useful for the production of difficult-to-access intermediates and pharmaceuticals. In this review, an overview of the progress achieved in asymmetric catalytic reactions of pyrazoleamides from 2015 up to middle 2020, is illustrated. Rearrangements of α-Diazo Pyrazoleamides 7. Combined Metal-and Organocatalysis 8. Pyrazoleamides in Visible-Light-Activated Photochemical Reactions 8.1. Merging Visible Light Photoredox Activation with Asymmetric Catalysis 8.2. Stereocontrolled Direct Photoreactions from Electronically Excited State 8.3. Merging HAT Photocatalysis with Chiral Lewis Acid Catalysis 9.

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Section: Pyrazoleamides As Electrophiles In Organocatalysismentioning

confidence: 99%

Pyrazoleamides in Catalytic Asymmetric Reactions: Recent Advances

et al. 2021

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“…bond formations [1][2][3][4][5]. Metal or metal-free catalyzed Michael additions have been well documented by many chemists [6][7][8][9][10]. The activated methylene compounds such as 1,3-dicarbonyl compounds, α-nitro-and α-cyanoesters are the most common Michael donors and used as pronucleophiles to attack electron-deficient alkenes in the presence of suitable catalysts [11][12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

DBU-catalyzed Michael addition of bulky glycine imine to α,β-unsaturated isoxazoles and pyrazolamides

Bai¹,

Cheng²,

Hu³

et al. 2021

Preprint

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A DBU-catalyzed Michael additions of several pronucleophiles with high pK a values including bulky glycine imines, α-tetra-lone, 1-methyl-2-indolone and nitroalkanes to α,β-unsaturated isoxazoles and pyrazolamides have been realized in THF with 1.0 eq. LiBr as a additive at room temperature within 3 h to provide Michael adducts in excellent yields (up to 97%) and diastereoselectivities (> 20:1).

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“…Metal–organic frameworks (MOFs) are documented as one of the most significant classes of porous materials due to their distinctive features and versatility . However, the development of water‐stable MOFs still remains a great challenge for applications, in terms of five major areas—adsorption and/or separation, sensing, catalysis, drug delivery, and proton conduction—where such applications are conducted in water‐containing environments .…”

Section: Introductionmentioning

confidence: 99%

A “Thermodynamically Stable” 2D Nickel Metal–Organic Framework over a Wide pH Range with Scalable Preparation for Efficient C₂s over C₁ Hydrocarbon Separations

Sahoo

Chand

Mondal

et al. 2020

Chemistry A European J

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The design and construction of "thermodynamically stable" metal-organic frameworks (MOFs) that can survive in liquid water,b oiling water,a nd acidic/basic solutions over aw ide pH range is highly desirable for many practicala pplications, especially adsorption-based gas separationsw ith obviouss calablep reparations. Herein,anew thermodynamically stable Ni MOF,{ [Ni(L)(1,4-NDC)(H 2 O) 2 ]} n (IITKGP-20;L= 4,4'-azobispyridine;1 ,4-NDC = 1,4-naphthalene dicarboxylic acid;I ITKGP stands for the Indian Institute of Technology Kharagpur), hasb een designed that displays moderate porosity with aB ET surfacea rea of 218 m 2 g À1 and micropores along the [10À1] direction. As an alternative to ac ost-intensive, cryogenic,h igh-pressure distillation process for the separation of hydrocarbons, MOFsh ave recently shown promise for such separations. Thus, towards an application standpoint, this MOF exhibits ah igher uptake of C 2 hydrocarbons over that of C 1 hydrocarbon under ambient conditions, with one of the highest selectivities basedo nt he ideal adsorbed solution theory (IAST)m ethod. Ac ombination of two strategies (the presence of stronger metal-N coordinationo ft he spacera nd the hydrophobicity of the aromatic moiety of the organic ligand) possibly makes the framework highly robust, even stable in boiling water and over aw ide range of pH 2-10, andr epresents the first example of at hermodynamically stableM OF displayinga2D structural network. Moreover, this material is easily scalable by heatingt he reaction mixture at reflux overnight. Because such separations are performedi nt he presence of water vapor and acidic gases, there is ag reat need to explore thermodynamically stable MOFs that retain not only structurali ntegrity,b ut also the porosityo ft he frameworks.

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Enantioselective Catalytic Reactions with N-Acyliden Penta-atomic Aza-heterocycles. Heterocycles as Masked Bricks To Build Chiral Scaffolds

Cited by 59 publications

References 139 publications

Pyrazoleamides in Catalytic Asymmetric Reactions: Recent Advances

Pyrazoleamides in Catalytic Asymmetric Reactions: Recent Advances

DBU-catalyzed Michael addition of bulky glycine imine to α,β-unsaturated isoxazoles and pyrazolamides

A “Thermodynamically Stable” 2D Nickel Metal–Organic Framework over a Wide pH Range with Scalable Preparation for Efficient C₂s over C₁ Hydrocarbon Separations

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Enantioselective Catalytic Reactions with N-Acyliden Penta-atomic Aza-heterocycles. Heterocycles as Masked Bricks To Build Chiral Scaffolds

Cited by 59 publications

References 139 publications

Pyrazoleamides in Catalytic Asymmetric Reactions: Recent Advances

Pyrazoleamides in Catalytic Asymmetric Reactions: Recent Advances

DBU-catalyzed Michael addition of bulky glycine imine to α,β-unsaturated isoxazoles and pyrazolamides

A “Thermodynamically Stable” 2D Nickel Metal–Organic Framework over a Wide pH Range with Scalable Preparation for Efficient C2s over C1 Hydrocarbon Separations

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A “Thermodynamically Stable” 2D Nickel Metal–Organic Framework over a Wide pH Range with Scalable Preparation for Efficient C₂s over C₁ Hydrocarbon Separations