Substituted <i>N</i>-Salicylidene β-Aminoalcohols: Preparation and use as Chiral Ligands in Enantioselective Sulfoxidation and Conjugate Addition

Skarżewski, Jacek; Ostrycharz, Elżbieta; Siedlecka, Renata; Zielińska-Błajet, Mariola; Pisarski, Bartłomiej

doi:10.3184/030823401103169847

Cited by 21 publications

(28 citation statements)

References 14 publications

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“…Methods of preparation of the hydrazides 4b-c and aldehydes of choice 6a-b, 6d-f, 7a-b, and 7d-f were adapted from the original literature [54][55][56][57][58][59][60][61][62][63][64]. 4-Methoxy-and 3-hydroxybenzoic acid hydrazides 4b and 4c were prepared in 67-85% yields from the appropriate benzoic acid methyl esters 8b and 8c and hydrazine monohydrate following a literature procedure [63].…”

Section: Syntheses and Characterizationsmentioning

confidence: 99%

Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor

et al. 2020

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A series of hydrazide-hydrazones 1–3, the imine derivatives of hydrazides and aldehydes bearing benzene rings, were screened as inhibitors of laccase from Trametes versicolor. Laccase is a copper-containing enzyme which inhibition might prevent or reduce the activity of the plant pathogens that produce it in various biochemical processes. The kinetic and molecular modeling studies were performed and for selected compounds, the docking results were discussed. Seven 4-hydroxybenzhydrazide (4-HBAH) derivatives exhibited micromolar activity Ki = 24–674 µM with the predicted and desirable competitive type of inhibition. The structure–activity relationship (SAR) analysis revealed that a slim salicylic aldehyde framework had a pivotal role in stabilization of the molecules near the substrate docking site. Furthermore, the presence of phenyl and bulky tert-butyl substituents in position 3 in salicylic aldehyde fragment favored strong interaction with the substrate-binding pocket in laccase. Both 3- and 4-HBAH derivatives containing larger 3-tert-butyl-5-methyl- or 3,5-di-tert-butyl-2-hydroxy-benzylidene unit, did not bind to the active site of laccase and, interestingly, acted as non-competitive (Ki = 32.0 µM) or uncompetitive (Ki = 17.9 µM) inhibitors, respectively. From the easily available laccase inhibitors only sodium azide, harmful to environment and non-specific, was over 6 times more active than the above compounds.

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Section: Syntheses and Characterizationsmentioning

confidence: 99%

Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor

et al. 2020

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“…[6] Skarzewski et al introduced Schiff bases with a phenyl substituent at C 3 of salicylaldehyde. [7] Anson et al reported that a vanadium-chiral Schiff base complex derived from 3,5-diiodosalicylaldehyde and (S)-t-leucinol was effective in the vanadium-catalyzed oxidation of alkyl aryl sulfides. [8] Ahn described the application of sterically hindered chiral Schiff base ligands that were prepared from chiral t-leucinol and aldehydes derived from binol for the oxidation of sulfides.…”

Section: Introductionmentioning

confidence: 99%

Vanadium‐Catalyzed Asymmetric Oxidation of Sulfides Using Schiff Base Ligands Derived from β‐Amino Alcohols with Two Stereogenic Centers

Liu

et al. 2009

Eur J Org Chem

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“…Bolm first reported the famous vanadium catalyst system prepared in situ from VO(acac) 2 and substituted with the salicylidene derivative ( S )‐ tert ‐leucinol in 1995, which effectively catalyzed the oxidation of sulfides to sulfoxides using hydrogen peroxide as the oxidant with good enantioselectivity (up to 80% ee ) 7. Since then many optimizations have been carried out on the basis of this protocol including: (i) the use of other amino alcohols for the preparation of Schiff bases as chiral ligands,8 (ii) ( S )‐ tert ‐leucinol‐based Schiff bases modified with various aromatic aldehydes,6,8a,9 (iii) the manner of H 2 O 2 addition and the use of additives,10 (iv) the method of oxidation/kinetic resolution 11…”

Section: Methodsmentioning

confidence: 99%

Enantioselective Vanadium‐Catalyzed Oxidation of 1,3‐Dithianes from Aldehydes and Ketones using β‐Amino Alcohol Derived Schiff Base Ligands

Mao

Meng

et al. 2011

Adv Synth Catal

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Abstract:The asymmetric vanadium-catalyzed oxidation of 1,3-dithianes from aldehydes and ketones by b-amino alcohol-derived Schiff base ligands with two stereogenic centers was investigated. Using aqueous hydrogen peroxide as the oxidant and the Schiff base 3b as a chiral ligand, a variety of 1,3-dithianes derived from aldehydes were easily converted into the corresponding mono-sulfoxides in good yields (81-88%) with excellent enantioselectivities (up to 99% ee). Additionally, 99% ee was obtained for the enantioselective vanadium-catalyzed oxidation of the 1,3-dithianes derived from ketones. We found a slight kinetic resolution when using a higher ratio of hydrogen peroxide during the oxidation of the aldehyde-derived 1,3-dithianes but not in the ketone-derived 1,3-dithianes.

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Substituted N-Salicylidene β-Aminoalcohols: Preparation and use as Chiral Ligands in Enantioselective Sulfoxidation and Conjugate Addition

Cited by 21 publications

References 14 publications

Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor

Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor

Vanadium‐Catalyzed Asymmetric Oxidation of Sulfides Using Schiff Base Ligands Derived from β‐Amino Alcohols with Two Stereogenic Centers

Enantioselective Vanadium‐Catalyzed Oxidation of 1,3‐Dithianes from Aldehydes and Ketones using β‐Amino Alcohol Derived Schiff Base Ligands

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