Cooperative Organocatalysis: A Systematic Investigation of Covalently Linked Organophosphoric Acids for the Stereoselective Transfer Hydrogenation of Quinolines

Thölke, Simon; Zhu, Hai‐Liang; Jansen, Dennis; Octa-Smolin, Frescilia; Thiele, Maike; Kaupmees, Karl; Leito, Ivo; Niemeyer, Jochen

doi:10.1002/ejoc.201900548

Cited by 9 publications

(12 citation statements)

References 87 publications

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“…Serving as a benchmark reactions, various procedures were reported for the asymmetric reduction of 2-phenylquinoline (49), relying on classical CPA catalysis in alternative reaction media, [55] bitetralone-modified CPAs, [56] cyclophane-and cathenane-based CPAs, [57][58][59] bisphosphoric acids, [60,61] as well as using BIFOL- [62] and SPINOL-derivatives (Scheme 19). [63] Tang et al explored a novel, AOX-mediated (AOX: aza-oxylene) methodology to access dihydroquinolines (Scheme 20).…”

Section: Asymmetric Transfer Hydrogenation Of N-heterocyclesmentioning

confidence: 99%

Chiral Phosphoric Acids as Versatile Tools for Organocatalytic Asymmetric Transfer Hydrogenations

et al. 2021

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Herein, recent developments in the field of organocatalytic asymmetric transfer hydrogenation (ATH) of C=N, C=O and C=C double bonds using chiral phosphoric acid catalysis are reviewed. This still rapidly growing area of asymmetric catalysis relies on metal-free catalysts in combination with biomimetic hydrogen sources. Chiral phosphoric acids have proven to be extremely versatile tools in this area, providing highly active and enantioselective alternatives for the asymmetric reduction of α,β-unsaturated carbonyl compounds, imines and various heterocycles. Eventually, such transformations are more and more often used in multicomponent/cascade reactions, which undoubtedly shows their great synthetic potential and the bright future of organocatalytic asymmetric transfer hydrogenations.

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Section: Asymmetric Transfer Hydrogenation Of N-heterocyclesmentioning

confidence: 99%

Chiral Phosphoric Acids as Versatile Tools for Organocatalytic Asymmetric Transfer Hydrogenations

et al. 2021

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“…We recently reported a series of multidentate phosphoric acids ( 1 d / e / f , Figure 1 for 1 d / e / f ) that feature two or three BINOL‐based phosphoric acid diesters of the type (ArO) 2 P(O)OH. These systems were applied in organocatalysis, [13] but also for the chemosensing of metal‐ions [14] and amino acids [15] . By an acid‐catalyzed cyclization, we also generated the furane‐annelated phosphoric acid monoesters 11 d / e / f , which possess two or three binding units of the type (ArO)P(O)(OH) 2 .…”

Section: Figurementioning

confidence: 99%

Development of Fluorescent Chemosensors for Amino‐Sugars

Yadav

Kwamen

Niemeyer

2021

Israel Journal of Chemistry

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In this account, we describe the application of a series of multidentate BINOL‐based phosphoric acids for the fluorescence‐based chemosensing of amino sugars. To this end, we developed a novel synthetic protocol for three isomerically pure phosphoric acid monoesters of the type ArOP(O)(OH)2. These were investigated with respect to their binding towards amino sugars (glucosamine, galactosamine and mannosamine) in comparison to the previously reported diesters of the type (ArO)2P(O)(OH). We could find that the diesters show no significant binding, while the monoesters can be used as hosts for amino sugars. Indeed, one host selectively binds to galactosamine, while a second host binds both glucosamine and mannosamine. This allows the fluorescence‐based detection and discrimination of the amino sugars by a novel class of phosphate‐based supramolecular hosts.

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“…In our work, we became interested in the synthesis of novel bis-BINOL derivatives for use in chemosensing, 18 supramolecular self-assembly, 19 and organocatalysis. 20 To generate bis-BINOL derivatives with different geometries, we envisaged linking via the 3-position (for a bent overall geometry) and via the 4-or 5-position (for a linear overall geometry) (see Figure 2). This required the synthesis of suitable C 1 -symmetric precursors for each position.…”

Section: Syn Thesismentioning

confidence: 99%

Synthesis of Bis-BINOL Derivatives: Linking via the 3-, 4-, or 5-Position by Generation of Suitable C 1-Symmetric Precursors

et al. 2019

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Bis-BINOL derivatives have proven highly useful in applications such as chemosensing or organocatalysis. In this account, we describe strategies for the linking of BINOL units via the 3-, 4-, or 5-positions, showing that unique synthetic strategies are necessary to address each position. We report the synthesis of suitable C 1-symmetric precursors, which are generated either by monohalogenation or by monodeprotection of C 2-symmetric starting materials, and their subsequent coupling to give linked bis-BINOL derivatives.

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Cooperative Organocatalysis: A Systematic Investigation of Covalently Linked Organophosphoric Acids for the Stereoselective Transfer Hydrogenation of Quinolines

Cited by 9 publications

References 87 publications

Chiral Phosphoric Acids as Versatile Tools for Organocatalytic Asymmetric Transfer Hydrogenations

Chiral Phosphoric Acids as Versatile Tools for Organocatalytic Asymmetric Transfer Hydrogenations

Development of Fluorescent Chemosensors for Amino‐Sugars

Synthesis of Bis-BINOL Derivatives: Linking via the 3-, 4-, or 5-Position by Generation of Suitable C 1-Symmetric Precursors

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