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5 article(s) from Nonn, Melinda

Synthesis of novel fluorinated building blocks via halofluorination and related reactions

Attila Márió Remete,
Tamás T. Novák,
Melinda Nonn,
Matti Haukka,
Ferenc Fülöp and
Loránd Kiss

Beilstein J. Org. Chem. 2020, 16, 2562–2575, doi:10.3762/bjoc.16.208

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Scheme 1: Proposed outcome of the halofluorination of (rac)-1. Only the main conformers of (rac)-1 and (rac)-...

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Scheme 2: Halofluorination reactions of the trans-diester (rac)-1.

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Scheme 3: Probable outcomes of the halofluorination of 4. Both conformers of the compounds 4, (rac)-T2a,b, an...

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Scheme 4: Halofluorination reactions of the cis-diester 4. Important NOESY interactions are indicated by two-...

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Scheme 5: Halofluorination reactions of the cis-tetrahydrophthalic imide derivative 7.

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Scheme 6: Synthesis and halofluorination of the trans-imide (rac)-10.

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Figure 1: Crystal structure of (rac)-11b.

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Scheme 7: Synthesis of the cyclic carbamide (rac)-13.

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Scheme 8: Halofluorination reactions of the γ-lactam (rac)-14. Relevant NOESY interactions are indicated by t...

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Figure 2: Crystal structure of the product (rac)-15a.

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Figure 3: Crystal structure of the product (rac)-15b.

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Scheme 9: Reactions of the diester 16 with NBS or NIS in the presence or absence of Deoxo-Fluor^®.

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Scheme 10: Formation of the halolactons (rac)-17a,b. The initial attack of the halogen cation occurs at the st...

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Scheme 11: Unsuccessful halofluorination of the bicyclic diester 18.

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Scheme 12: Halofluorination reactions of the rigid tricyclic imine 19. The relevant NOESY interactions are mar...

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Scheme 13: Mechanism of the halofluorination reactions of the substrate 19. X = Br (compounds a), I (compounds...

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Scheme 14: Synthesis and halofluorination of the imide 24.

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Scheme 15: Cyclizations of halofluorinated diesters with potassium tert-butoxide. Relevant NOESY interactions ...

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Scheme 16: Mechanism of the reaction of the cyclopropanation of the compounds (rac)-2a,b and (rac)-5a with t-B...

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Scheme 17: Presumed mechanism of the reaction of the compound (rac)-6b with t-BuOK.

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Scheme 18: Cyclizations of halofluorinated tetrahydrophthalimides with DBU. Relevant NOESY interactions are ma...

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Scheme 19: Mechanism for the formation of (rac)-28 from (rac)-11a,b. Although the formation of the compound (r...

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Scheme 20: Fluoroselenations of the cyclohexenedicarboxylates (rac)-1 and 4.

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Scheme 21: PhSe⁺-induced lactonization of the diester 16. Relevant NOESY interactions are marked with two-head...

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Scheme 22: Oxidation of the fluoroselenide (rac)-30 under acidic and basic conditions.

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Scheme 23: Oxidation of the fluoroselenide mixture (rac)-31 under acidic and basic conditions.

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Published 16 Oct 2020

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Ring-opening metathesis of some strained bicyclic systems; stereocontrolled access to diolefinated saturated heterocycles with multiple stereogenic centers

Zsanett Benke,
Melinda Nonn,
Márton Kardos,
Santos Fustero and
Loránd Kiss

Beilstein J. Org. Chem. 2018, 14, 2698–2707, doi:10.3762/bjoc.14.247

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Scheme 1: ROM of various bicyclic unsaturated β-lactams [14-16].

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Scheme 2: ROM of various constrained bicyclic unsaturated systems (γ-lactones, δ-lactones, γ-lactam, isoxazol...

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Figure 1: Commercial Ru-based catalysts used in the current work.

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Scheme 3: ROM of lactones (±)-3 and (±)-4.

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Scheme 4: ROM of lactones (±)-9.

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Scheme 5: ROM of structurally constrained bicyclic lactones and lactams.

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Scheme 6: ROM of bridged lactone (±)-14 and cyclooctene-fused isoxazoline (±)-16.

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Scheme 7: ROM and transformations of lactam (±)-18.

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Figure 2: Chelate intermediates in CM of (±)-19.

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Published 24 Oct 2018

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Fluorination of some highly functionalized cycloalkanes: chemoselectivity and substrate dependence

Attila Márió Remete,
Melinda Nonn,
Santos Fustero,
Matti Haukka,
Ferenc Fülöp and
Loránd Kiss

Beilstein J. Org. Chem. 2017, 13, 2364–2371, doi:10.3762/bjoc.13.233

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Scheme 1: Fluorination of diol derivative (±)-1.

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Scheme 2: Fluorination of diol derivative (±)-4.

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Figure 1: X-ray structure of fluorohydrine derivative (±)-5.

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Scheme 3: Fluorination of diol derivative (±)-6.

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Scheme 4: Fluorination of cyclohexane-derived diol (±)-8.

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Scheme 5: Proposed route for the formation of compounds (±)-10 and (±)-11.

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Scheme 6: Fluorination of diol derivative (±)-12.

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Scheme 7: Fluorination of diol derivative (±)-14.

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Scheme 8: Proposed route for the formation of compounds (±)-15, (±)-16 and (±)-17.

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Scheme 9: Fluorination of N-Cbz-protected diol derivative (±)-18.

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Scheme 10: Fluorination of diol derivative (±)-20.

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Scheme 11: Fluorination of meso diol derivative 24.

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Published 06 Nov 2017

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Efficient regio- and stereoselective access to novel fluorinated β-aminocyclohexanecarboxylates

Loránd Kiss,
Melinda Nonn,
Reijo Sillanpää,
Santos Fustero and
Ferenc Fülöp

Beilstein J. Org. Chem. 2013, 9, 1164–1169, doi:10.3762/bjoc.9.130

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Scheme 1: Synthesis of all-cis ethyl 4-hydroxylated β-aminocyclohexanecarboxylate 5.

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Figure 1: ORTEP diagram of iodooxazinone 2. Thermal ellipsoids have been drawn at the 20 % probability level.

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Figure 2: ORTEP diagram of hydroxylated amino ester 5. Thermal ellipsoids have been drawn at the 20% probabil...

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Scheme 2: Syntheses of fluorinated amino esters 7 and 9.

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Scheme 3: Synthesis of ethyl 4-hydroxy-β-aminocyclohexanecarboxylate 14.

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Figure 3: ORTEP diagram of iodooxazinone derivative 12. Thermal ellipsoids have been drawn at the 20% probabi...

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Figure 4: ORTEP diagram of hydroxylated amino ester 14. The water molecule oxygen atom O4 is situated on the ...

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Scheme 4: Syntheses of fluorinated amino esters 16 and 18.

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Published 17 Jun 2013

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Synthesis of highly functionalized β-aminocyclopentanecarboxylate stereoisomers by reductive ring opening reaction of isoxazolines

Melinda Nonn,
Loránd Kiss,
Reijo Sillanpää and
Ferenc Fülöp

Beilstein J. Org. Chem. 2012, 8, 100–106, doi:10.3762/bjoc.8.10

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Figure 1: Structures of neuraminidase inhibitors.

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Scheme 1: Isoxazoline-fused β-aminocyclopentanecarboxylate regio- and stereoisomers [8].

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Scheme 2: Treatment of isoxazoline-fused amino ester 2 with NaBH₄.

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Scheme 3: Reduction with Pd/C in the presence of HCO₂NH₄.

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Scheme 4: Transformation of isoxazoline-fused cispentacin stereoisomer 2 into multifunctionalized β-amino aci...

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Figure 2: ORTEP diagram of 12 showing the atomic labeling scheme. The thermal ellipsoids are drawn at the 20%...

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Scheme 5: Synthesis of multifunctionalized β-amino acid derivatives 13–16. Reaction conditions: NaBH₄, NiCl₂,...

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Published 17 Jan 2012

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