<i>trans</i>‐Cyclooctenes as Halolactonization Catalysts

Einaru, Shunsuke; Shitamichi, Kenta; Nagano, Tagui; Matsumoto, Akira; Asano, Keisuke; Matsubara, Seijiro

doi:10.1002/ange.201808320

Cited by 6 publications

(2 citation statements)

References 57 publications

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“…We then investigated the catalytic activity of 10a toward the bromolactonization of the alkenoic acid 15 (Table 3 ). In our previous work, we developed monosubstituted TCOs as catalysts for bromolactonization (Table 3 , entries 2 and 3) 8a and found that the substituents on the TCOs have significant effects on the catalytic activity; we identified 17 bearing a benzyl group as the most active catalyst. The investigation of the catalytic efficiency of 10a bearing two benzyl groups revealed that 10a was superior to 17 (Table 3 , entry 1).…”

Section: Table 1 Optimization Of the Cross-coupling Of ...mentioning

confidence: 99%

Synthesis of Substituted Cyclooctenes through Cross-Coupling Reactions

Uraguchi,

Asano,

Murata

et al. 2024

Synlett

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Cross-coupling methods for the introduction of various substituents into the olefin moiety of cyclooctenes were developed. A range of 1-substituted cis-cyclooctenes were synthesized. These protocols unlocked routes to previously inaccessible derivatives, allowing for the syntheses of cis-cyclooctenes bearing various functional groups. Moreover, the method was applied to the synthesis of a 1,2-disubstituted trans-cyclooctene for the first time, which proved to be a significantly active organocatalyst in relation to the previously developed monosubstituted trans-cyclooctene.

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Section: Table 1 Optimization Of the Cross-coupling Of ...mentioning

confidence: 99%

Synthesis of Substituted Cyclooctenes through Cross-Coupling Reactions

Uraguchi,

Asano,

Murata

et al. 2024

Synlett

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“…[4b,4c] However, to the best of our knowledge, the behavior of trans-cyclooctene derivatives as chiral ligands for asymmetric catalysis is unknown despite their potential as novel molecular-catalyst platforms. [6] Here, we introduce transcyclooctenes as asymmetric ligands for the rhodium-catalyzed 1,4-additions of organotin reagents and describe their performance, thereby providing new chiral platforms for asymmetric catalysis.…”

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confidence: 99%

trans‐Cyclooctenes as Chiral Ligands in Rhodium‐Catalyzed Asymmetric 1,4‐Additions

et al. 2020

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trans‐Cyclooctenes serve as asymmetric ligands for the rhodium‐catalyzed 1,4‐additions of organotin reagents to enones. We demonstrate, for the first time, that these chiral olefins can provide efficient coordination spheres for asymmetric metal catalysis. As the asymmetric environment around the reaction site is constructed by the trans‐cyclooctene framework, the introduction of a substituent at the allylic position further improves enantioselectivity to 93 % ee. These findings provide new chiral framework designs for the asymmetric ligands of metal catalysts.

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Metal‐ and Oxidant‐Free Electrosynthesis of Heterocycles from 1,2‐Diarylalkene Derivatives

Park

Kim

2022

Adv Synth Catal

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Synthesis of heterocycles from 1,2‐diarylalkene derivatives through electrosynthesis under metal‐ and oxidant‐free conditions has been discovered. Cathodic reduction of 2‐alkenylbenzoic acid or anodic oxidation of 2‐alkenylbenzamide, 2‐alkenylphenol and 2‐alkenylaniline leads to the formation of reactive radical intermediates which afford corresponding phthalide, isochroman‐1‐one, isoindolin‐1‐one, benzofuran, and indole in satisfying yields with good functional group tolerance. Interestingly, different chemoselectivities were found in different reaction solvents. Several mechanistic investigations including cyclic voltammetry studies and control experiments were carried out to elucidate the reaction mechanisms.

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trans‐Cyclooctenes as Halolactonization Catalysts

Cited by 6 publications

References 57 publications

Synthesis of Substituted Cyclooctenes through Cross-Coupling Reactions

Synthesis of Substituted Cyclooctenes through Cross-Coupling Reactions

trans‐Cyclooctenes as Chiral Ligands in Rhodium‐Catalyzed Asymmetric 1,4‐Additions

Metal‐ and Oxidant‐Free Electrosynthesis of Heterocycles from 1,2‐Diarylalkene Derivatives

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