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4 article(s) from Svoboda, Jan

Eschenmoser coupling reactions starting from primary thioamides. When do they work and when not?

Lukáš Marek,
Jiří Váňa,
Jan Svoboda and
Jiří Hanusek

Beilstein J. Org. Chem. 2023, 19, 808–819, doi:10.3762/bjoc.19.61

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Scheme 1: Eschenmoser coupling reaction between 3-substituted oxindoles and thioamides.

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Scheme 2: Possible reactions of α-haloketones, esters and amides with primary thioamides.

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Figure 1: Studied α-bromoamides and α-bromolactams.

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Scheme 3: Reaction of 4-bromo-1,1-dimethyl-1,4-dihydroisoquinolin-3(2H)-one (2b) with thiobenzamide and thioa...

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Scheme 4: Reaction of 4-bromo-1,1-dimethyl-1,4-dihydroisoquinolin-3(2H)-one (2b) with 4’-substituted thiobenz...

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Scheme 5: Reaction of 4-bromoisoquinoline-1,3(2H,4H)-dione (3) with thiobenzamide, thioacetamide, and thioben...

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Scheme 6: Reaction of N-phenyl- and N-methyl-2-bromo(phenyl)acetamide (4a,b) with thiobenzamide in acetonitri...

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Scheme 7: Transformation of salt 15 under kinetic and thermodynamic control conditions [1].

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Figure 2: Comparison of energy profiles (relative Gibbs energies at 298 K in kJ·mol⁻¹ for the ECR (right) and...

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Published 09 Jun 2023

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The asymmetric Henry reaction as synthetic tool for the preparation of the drugs linezolid and rivaroxaban

Martin Vrbický,
Karel Macek,
Jaroslav Pochobradský,
Jan Svoboda,
Miloš Sedlák and
Pavel Drabina

Beilstein J. Org. Chem. 2022, 18, 438–445, doi:10.3762/bjoc.18.46

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Figure 1: The structure of the oxazolidine-2-one-containing drugs linezolid (1) and rivaroxaban (2).

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Figure 2: Overview of the chiral ligands that were used for the study of the asymmetric Henry reaction.

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Scheme 1: Syntheses of aldehydes 15–20.

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Scheme 2: Synthesis of linezolid (1) and rivaroxaban (2) from nitroaldols 24 or 26.

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Published 14 Apr 2022

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Recent advances in palladium-catalysed asymmetric 1,4–additions of arylboronic acids to conjugated enones and chromones

Jan Bartáček,
Jan Svoboda,
Martin Kocúrik,
Jaroslav Pochobradský,
Alexander Čegan,
Miloš Sedlák and
Jiří Váňa

Beilstein J. Org. Chem. 2021, 17, 1048–1085, doi:10.3762/bjoc.17.84

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Scheme 1: Synthesis of optically pure 4-phenylchroman-2-one [34].

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Scheme 2: Synthesis of (R)-tolterodine [3].

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Scheme 3: Catalytic cycle of the Pd(II)-catalysed 1,4-addition of organoboron reagents to enones [3,26,35].

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Scheme 4: Enantioselective β-arylation of cyclohexanone [38].

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Scheme 5: Application of L2/Pd(OAc)₂ in the total synthesis of terpenes [8].

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Scheme 6: Plausible catalytic cycle for the addition of phenylboronic acid to 2-cyclohexenone catalysed by L3...

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Scheme 7: Microwave-assisted addition of phenylboronic acid to 2-cyclohexenone catalysed by L4/Pd₂(dba)₃·CHCl₃...

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Scheme 8: Plausible catalytic cycle of the addition of phenylboronic acid to 2-cyclohexenone catalysed by pal...

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Scheme 9: Proposed catalytic cycle for the addition of phenylboronic acids to 2-cyclohexenone catalysed by Pd...

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Scheme 10: Usage of addition reactions of boronic acids to various chromones in the syntheses of potentially a...

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Scheme 11: Multigram-scale synthesis of ABBV-2222 [6].

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Scheme 12: Application of the asymmetric addition of phenylboronic acid to a chromone derivative for the total...

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Scheme 13: Plausible catalytic cycle for the addition of phenylboronic acid to 3-methyl-2-cyclohexenone cataly...

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Scheme 14: Total syntheses of naturally occurring terpenoids [10,11].

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Scheme 15: Use of the L9/Pd(TFA)₂ catalytic system for the synthesis of intermediates of biologically active c...

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Scheme 16: Usage of a Michael addition catalysed by L9/Pd(TFA)₂ in the total synthesis of (–)-ar-tenuifolene [12].

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Scheme 17: Synthesis of terpenoids by Michael addition to 3-methyl-2-cyclopentenone [13].

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Scheme 18: Rh-catalysed isomerisation of 3-alkyl-3-arylcyclopentanones to 1-tetralones [53].

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Scheme 19: Addition reaction of phenylboronic acid to 3-methyl-2-cyclohexenone catalysed by L9/Pd(TFA)₂ in wat...

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Scheme 20: Micellar nanoreactor PdL10c for the synthesis of flavanones [58].

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Scheme 21: Plausible catalytic cycle for the desymmetrisation of polycyclic cyclohexenediones by the addition ...

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Scheme 22: Attempt to use the catalytic system L2/Pd(TFA)₂ for the addition of phenylboronic acid to 3-methyl-...

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Scheme 23: Ring opening of an enantioenriched tetrahydropyran-2-one derivative as alternative strategy to line...

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Scheme 24: Synthesis of biologically active compounds from addition products [14-16].

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Scheme 25: Chiral 1,10-phenantroline derivative L15 as ligand for the Pd-catalysed addition reactions of pheny...

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Scheme 26: The Rh-catalysed addition reaction of phenylboronic acid to a 3-substituted enone [20].

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Scheme 27: Underdeveloped methodologies [14,15,65-67].

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Scheme 28: Flowchart for the selection of the proper catalytic system.

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Published 10 May 2021

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Synthesis of (Z)-3-[amino(phenyl)methylidene]-1,3-dihydro-2H-indol-2-ones using an Eschenmoser coupling reaction

Lukáš Marek,
Lukáš Kolman,
Jiří Váňa,
Jan Svoboda and
Jiří Hanusek

Beilstein J. Org. Chem. 2021, 17, 527–539, doi:10.3762/bjoc.17.47

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Figure 1: Nintedanib ethanesulfonate.

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Scheme 1: The known synthetic strategies leading to 3-(aminomethylidene)oxindoles.

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Scheme 2: The possible intermediates and products occurring in the reactions of 3-bromooxindoles with thioben...

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Figure 2: The R¹ and R² substitution influence on the isolated yields of products 5aa–ed.

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Scheme 3: The Eschenmoser coupling reaction of 3-bromooxindole (1a) with thioacetamides.

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Scheme 4: The synthesis of alternative 3-substituted oxindoles and their Eschenmoser coupling reaction with t...

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Published 23 Feb 2021

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