Synthesis of Chiral Polyethers Containing Imidazolidinone Repeating Units and Application as Catalyst in Asymmetric Diels–Alder Reaction

Itsuno, Shinichi; Oonami, Tatsuaki; Takenaka, Nagisa; Haraguchi, Naoki

doi:10.1002/adsc.201500539

Cited by 18 publications

(13 citation statements)

References 29 publications

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“…Boc-L-tyrosine (5) [41] L-tyrosine (8.80 g, 48.6 mmol) and NaOH (3.89 g, 97.2 mmol) were dissolved in a mixture of 1,4dioxane (100 mL) and water (100 mL). The solution was cooled to 0°C prior to the addition of Boc 2 O 13 1H, pyrrole-NH) ppm.…”

Section: Supporting Informationmentioning

confidence: 99%

Design, Synthesis, and Evaluation of Novel Tyrosine‐Based DNA Gyrase B Inhibitors

Cotman

Trampuž

Brvar

et al. 2017

Archiv der Pharmazie

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The discovery and synthesis of new tyrosine-based inhibitors of DNA gyrase B (GyrB), which target its ATPase subunit, is reported. Twenty-four compounds were synthesized and evaluated for activity against DNA gyrase and DNA topoisomerase IV. The antibacterial properties of selected GyrB inhibitors were demonstrated by their activity against Staphylococcus aureus and Enterococcus faecalis in the low micromolar range. The most promising compounds, 8a and 13e, inhibited Escherichia coli and S. aureus GyrB with IC values of 40 and 30 µM. The same compound also inhibited the growth of S. aureus and E. faecalis with minimal inhibitory concentrations (MIC ) of 14 and 28 µg/mL, respectively.

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Section: Supporting Informationmentioning

confidence: 99%

Design, Synthesis, and Evaluation of Novel Tyrosine‐Based DNA Gyrase B Inhibitors

Cotman

Trampuž

Brvar

et al. 2017

Archiv der Pharmazie

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“…Importantly, a few of these main‐chain polymers exhibit higher enantioselectivity than that of model organocatalysts when tested in asymmetric reactions . Despite the importance of tuning the structure of the main‐chain repeat unit, the influence of chiral imidazolidinone dimers and disulfonate components in main‐chain polymers of chiral imidazolidinone salts on asymmetric reactions has not been comprehensively investigated .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Main‐Chain Ionic Polymers of Chiral Imidazolidinone Organocatalysts and Their Application to Asymmetric Diels–Alder Reactions

et al. 2017

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Main-chain ionic polymersi ncorporating chiral imidazolidinonem oieties in the polymer main chain were successfully synthesizedb yt he polyaddition reactiono fachiral imidazolidinoned imer with ad isulfonica cid. Theo rganocatalytic activities of these polymersw ere investigated in the asymmetric Diels-Alder reactionb etween trans-cinnamaldehyde and 1,3-cyclopentadiene.T he catalytic performance of the polymers was found to be sensitive to the chemical structure of the disulfonate units andt he imidazolidinone dimer. With the use of these heterogeneousp olymeric chiral organocatalysts, enantioselectivities of up to 99% for the endo isomer were obtained.T his result was higher than those obtained with corresponding monomeric andd imeric counterparts in ah omogeneouss olution. Thep olymeric chiral organocatalyst was recovered and reused several times,m aintaining its high enantioselectivity.

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“…Recently, we developed polymers incorporating a chiral organocatalyst into the polymer main chain . A polyether incorporating chiral imidazolidinone into the polymer main chain has been prepared by the Williamson reaction of a bisphenol‐type chiral imidazolidinone monomer with an achiral dihalide, followed by the addition of an acid .…”

Section: Introductionmentioning

confidence: 99%

Polyesters Containing Chiral Imidazolidinone Salts in Polymer Main Chain: Heterogeneous Organocatalysts for the Asymmetric Diels–Alder Reaction

2017

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Novel main‐chain polyesters functionalized with chiral imidazolidinone salts were successfully synthesized. Polycondensation of a chiral imidazolidinone dimer bearing two hydroxyphenyl groups with selected achiral dicarboxylic acid chlorides followed by the addition of an acid afforded polyesters with chiral imidazolidinone salts incorporated into the polymer main chain. Main‐chain ionic polyesters functionalized with chiral imidazolidinone salts in the polymer main chain were synthesized by the neutralization polymerization of a chiral imidazolidinone dimer with selected aromatic disulfonic acids. These polyesters were used as heterogeneous organocatalysts in the asymmetric Diels–Alder reaction of trans‐cinnamaldehyde and 1,3‐cyclopentadiene. By optimizing the polymer main‐chain structure, enantioselectivity of up to 97 % was achieved, which is higher than that attained using the corresponding monomeric and dimeric chiral imidazolidinone salts. These heterogeneous organocatalysts were easily recovered from the reaction mixture and reused several times without significant loss of the enantioselectivity.

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Synthesis of Chiral Polyethers Containing Imidazolidinone Repeating Units and Application as Catalyst in Asymmetric Diels–Alder Reaction

Cited by 18 publications

References 29 publications

Design, Synthesis, and Evaluation of Novel Tyrosine‐Based DNA Gyrase B Inhibitors

Design, Synthesis, and Evaluation of Novel Tyrosine‐Based DNA Gyrase B Inhibitors

Synthesis of Main‐Chain Ionic Polymers of Chiral Imidazolidinone Organocatalysts and Their Application to Asymmetric Diels–Alder Reactions

Polyesters Containing Chiral Imidazolidinone Salts in Polymer Main Chain: Heterogeneous Organocatalysts for the Asymmetric Diels–Alder Reaction

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