Novel Ir-SYNPHOS<sup>®</sup> and Ir-DIFLUORPHOS<sup>®</sup> Catalysts for Asymmetric Hydrogenation of Quinolines

Deport, Coralie; Buchotte, Marie; Abecassis, Keren; Tadaoka, Hiroshi; Ayad, Tahar; Ohshima, Takashi; Genêt, J. P.; Mashima, Kazushi; Ratovelomanana‐Vidal, Virginie

doi:10.1055/s-2007-991076

Cited by 12 publications

(2 citation statements)

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“…In general, these methods include, inter alia, metal complexes with chiral ligands, such as the chiral catalysts Ir/MeO-Biphep/I 2 , 19 [IrCl(cod)] 2 /(S)-SEGPHOS, 20 Ru(OTf)(Ts-DPEN)(η 6 -cymene) complex, 21 and Ru(II) complexes, 22 among others. [23][24][25][26][27][28][29] Nevertheless, other approaches toward the enantioselective synthesis of compounds carrying the THQ scaffold have been reported. For instance, the synthesis of (-)-angustureine and (-)-cuspareine was accomplished by using high regio-and enantioselective intermolecular iridiumcatalyzed allylic amination 30,31 and conjugated addition of lithium (R)-N-phenyl-N-(-methylbenzyl)amide to an ,unsaturated 4-methoxyphenyl ester 32 as key steps.…”

Section: Paper Synthesismentioning

confidence: 99%

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Chemoenzymatic Enantioselective Synthesis of the Hancock Alkaloids (S)- and (R)-Galipeine, (S)-Cuspareine, (S)-Galipinine, and (S)-Angustureine

et al. 2022

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The enantioselective synthesis of the Hancock 1,2,3,4-tetrahydroquinoline alkaloids (S)-galipeine, (S)-cuspareine, (S)-galipinine, and (S)-angustureine and the non-natural enantiomer (R)-galipeine is described herein. The target compounds were obtained in 5 steps from a racemic quinaldinic acid-derived α-amino ester in overall yields of 21.2% to 37.5%. The synthetic route comprised two key steps: an enzymatic kinetic resolution to control the C-2 stereocenter, affording (S)- and (R)-α-amino esters as key chiral intermediates with 94% and 72% ee, respectively, and Wittig olefination of (R)- and (S)-α-amino aldehyde synthons with the corresponding phosphonium salts using a phase transfer system (t-BuOH/CH2Cl2), thereby allowing the introduction of alkyl substituents at C-2. Finally, the enantioselective synthesis was concluded with the catalytic hydrogenation of olefinic bonds on Wittig adducts to furnish the target Hancock alkaloids, including (R)-galipeine, whose synthesis is described here for the first time.

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confidence: 99%

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confidence: 99%

Chemoenzymatic Enantioselective Synthesis of the Hancock Alkaloids (S)- and (R)-Galipeine, (S)-Cuspareine, (S)-Galipinine, and (S)-Angustureine

et al. 2022

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Advances in the reduction of quinolines to 1,2,3,4‐tetrahydroquinolines

El‐Shahat

2021

Journal of Heterocyclic Chem

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The pursuit of modern sustainable chemistry has stimulated the development of innovative catalytic processes that enable chemical transformations to be performed under mild and clean conditions with high efficiency. Herein, we report that the hydrogenation of heteroaromatic compounds is one of the most efficient methods for the construction of heterocyclic skeletons, and only a few promising progress has been achieved. Transition metal‐catalyzed, a countless number of transition metals include have been used toward the development of homo/heterogeneous hydrogenation of quinolines via the most convenient route (Direct Hydrogenation) to obtain the corresponding tetrahydroquinoline derivatives.

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Advances in Transition Metal-Catalyzed Asymmetric Hydrogenation of Heteroaromatic Compounds

Song

Fan

2013

Stereoselective Formation of Amines

119

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Transition metal-catalyzed asymmetric hydrogenation of heteroaromatic compounds is undoubtedly a straightforward and environmentally friendly method for the synthesis of a wide range of optically active heterocyclic compounds, which are widespread and ubiquitous in naturally occurring and artificial bioactive molecules. Over the past decade, a number of transition metal (Ir, Rh, Ru, and Pd) catalysts bearing chiral phosphorus ligands, amine-tosylamine ligands, and N-heterocyclic carbene ligands have been developed for such challenging transformation. This review will describe the significant contributions concerning the transition metal-catalyzed asymmetric hydrogenation of N-, O-, and S-containing heteroaromatic compounds, with emphasis on the evolution of different chiral ligands, related catalyst immobilization, and mechanism investigations.

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Novel Ir-SYNPHOS^® and Ir-DIFLUORPHOS^® Catalysts for Asymmetric Hydrogenation of Quinolines

Abstract: Novel Ir-SYNPHOS and Ir-DIFLUORPHOS catalysts were synthesized and used for the synthesis of tetrahydroquinolines via asymmetric hydrogenation of the corresponding quinoline derivatives.

Cited by 12 publications

References 2 publications

Chemoenzymatic Enantioselective Synthesis of the Hancock Alkaloids (S)- and (R)-Galipeine, (S)-Cuspareine, (S)-Galipinine, and (S)-Angustureine

Chemoenzymatic Enantioselective Synthesis of the Hancock Alkaloids (S)- and (R)-Galipeine, (S)-Cuspareine, (S)-Galipinine, and (S)-Angustureine

Advances in the reduction of quinolines to 1,2,3,4‐tetrahydroquinolines

Advances in Transition Metal-Catalyzed Asymmetric Hydrogenation of Heteroaromatic Compounds

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Novel Ir-SYNPHOS® and Ir-DIFLUORPHOS® Catalysts for Asymmetric Hydrogenation of Quinolines

Abstract: Novel Ir-SYNPHOS and Ir-DIFLUORPHOS catalysts were synthesized and used for the synthesis of tetrahydroquinolines via asymmetric hydrogenation of the corresponding quinoline derivatives.

Cited by 12 publications

References 2 publications

Chemoenzymatic Enantioselective Synthesis of the Hancock Alkaloids (S)- and (R)-Galipeine, (S)-Cuspareine, (S)-Galipinine, and (S)-Angustureine

Chemoenzymatic Enantioselective Synthesis of the Hancock Alkaloids (S)- and (R)-Galipeine, (S)-Cuspareine, (S)-Galipinine, and (S)-Angustureine

Advances in the reduction of quinolines to 1,2,3,4‐tetrahydroquinolines

Advances in Transition Metal-Catalyzed Asymmetric Hydrogenation of Heteroaromatic Compounds

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Novel Ir-SYNPHOS^® and Ir-DIFLUORPHOS^® Catalysts for Asymmetric Hydrogenation of Quinolines