A highly enantio- and diastereoselective direct aldol reaction in aqueous medium catalyzed by thiazolidine-based compounds

Rambo, Raoní Scheibler; Jacoby, Caroline Gross; Silva, Tiago Lima da; Schneider, Paulo H.

doi:10.1016/j.tetasy.2015.04.010

Cited by 19 publications

(4 citation statements)

References 34 publications

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“… 12 They have additionally wide applications in the preparation of heterocyclic compounds and other organic molecules. 13 Recently, thioureas have been employed as ligands and organocatalysts in a diversity of asymmetric organic syntheses. 14 Moreover, they have been used in the manufacture of polymer 15 and as sensors for heavy metal detection.…”

Section: Introductionmentioning

confidence: 99%

A sustainable strategy for the synthesis of bis-2-iminothiazolidin-4-ones utilizing novel series of asymmetrically substituted bis-thioureas as viable precursors

Arafa

Ibrahim

2018

RSC Adv.

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Section: Introductionmentioning

confidence: 99%

A sustainable strategy for the synthesis of bis-2-iminothiazolidin-4-ones utilizing novel series of asymmetrically substituted bis-thioureas as viable precursors

Arafa

Ibrahim

2018

RSC Adv.

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“…[18] Figure 1 illustrates some of these compounds with the thiazolidine unit highlighted. Furthermore, thiazolidinic derivatives have been successfully applied in organocatalytic asymmetric direct aldol addition [19][20][21] and as chiral ionic liquids to produce chiral secondary alcohols with excellent enantiomeric excesses. [22] In parallel with the interest in thiazolidines, the study of 1,2,3-triazoles has also gained prominence for similar reasons: their diverse applications, both in pharmacology [23][24][25] and materials science.…”

Section: Introductionmentioning

confidence: 99%

“…Figure 1 illustrates some of these compounds with the thiazolidine unit highlighted. Furthermore, thiazolidinic derivatives have been successfully applied in organocatalytic asymmetric direct aldol addition [19–21] and as chiral ionic liquids to produce chiral secondary alcohols with excellent enantiomeric excesses [22]…”

Section: Introductionmentioning

confidence: 99%

Organocatalytic Synthesis and DNA Interactive Studies of New 1,2,3‐triazolyl‐thiazolidines Hybrids

Larroza,

Soares,

Morais

et al. 2024

ChemBioChem

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An organocatalytic [3 + 2] cycloaddition reaction between thiazolidine‐containing β‐ketoester 1 and aryl azides 2 was employed to synthesize new 1,2,3‐triazolyl‐thiazolidine hybrids 3. In this metal‐free approach, twelve compounds were isolated in yields ranging from 23% to 96% by using diethylamine (10 mol%) and DMSO at 75 °C for 24 hours. DNA‐binding assays were conducted through absorption, emission spectroscopy and viscosimetry analysis, to evaluate the interaction capacity of the studied derivatives with nucleic acids. All the synthesized compounds were evaluated for their interactions with a specific group of compounds containing the pharmacophoric groups triazole and thiazolidine through a molecular docking speculative study, aimed at identifying the interaction profile of these compounds with DNA. The obtained results suggest that 1,2,3‐triazolyl‐thiazolidine hybrids could be a promising approach in the development of novel therapeutic agents targeting DNA‐related processes.

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“…[14] More recently, Schneider et al developed several chiral thiazolidine-derived organocatalysts that were used in aldol reactions. [15,16] In this context, and in the continuation of our studies on the use of thiazolidines for asymmetric catalysis, [17] a series of new thiazolidine organocatalysts were synthesized and tested in asymmetric aldolic reactions. The results of these studies are described in this paper.…”

Section: Introductionmentioning

confidence: 99%

Chiral Thiazolidine based Organocatalysts: Synthesis and Application in Asymmetric Aldol Reactions

Félix

Simões

Sousa

et al. 2020

LOC

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Several novel chiral organocatalysts derived from thiazolidines containing amide and thioureia functionalities were synthesized in good yields. These organocatalysts were tested in the asymmetric aldol reaction of acetone with p-nitrobenzaldehyde. Reaction parameters such as reaction time, catalyst loading and solvent were optimized. Products with conversions up to 84% and enantiomeric ratios (er) up to 84.5:15.5 (R:S) were obtained. The effect of several chiral and non-chiral additives on the reactivity and selectivity of the reaction was also evaluated. The reaction was extended to other aromatic aldehydes with the best organocatalyst and when p-bromobenzaldehyde was used, an er of 94.5:5.5 (R:S) was obtained.

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A highly enantio- and diastereoselective direct aldol reaction in aqueous medium catalyzed by thiazolidine-based compounds

Cited by 19 publications

References 34 publications

A sustainable strategy for the synthesis of bis-2-iminothiazolidin-4-ones utilizing novel series of asymmetrically substituted bis-thioureas as viable precursors

A sustainable strategy for the synthesis of bis-2-iminothiazolidin-4-ones utilizing novel series of asymmetrically substituted bis-thioureas as viable precursors

Organocatalytic Synthesis and DNA Interactive Studies of New 1,2,3‐triazolyl‐thiazolidines Hybrids

Chiral Thiazolidine based Organocatalysts: Synthesis and Application in Asymmetric Aldol Reactions

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