Oxone-promoted hydration of electron-deficient allenic esters and ketones into 1,3-dicarbonyl compounds

Yi, Yu‐Ping; Zheng, Yan; Nie, Jing; Ma, Jun‐An

doi:10.1016/j.tetlet.2015.05.120

Cited by 4 publications

(3 citation statements)

References 37 publications

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“…Interestingly, allenones 2 react in the presence of indium to generate an alkenylindium dimer which can be further trapped through a palladium‐catalyzed cross‐coupling reaction with aryl iodides 579 affording substituted enones 580 (Scheme 98d) [244] . Hydroxylation of α‐allenones 2 has also been reported in the context of a more general conjugate addition to cumulenes, providing hydroxyl alkenes 581 from allenones 2 and Oxone (Scheme 98e) [245] …”

Section: Synthetic Utilitymentioning

confidence: 99%

“…[244] Hydroxylation of α-allenones 2 has also been reported in the context of a more general conjugate addition to cumulenes, providing hydroxyl alkenes 581 from allenones 2 and Oxone (Scheme 98e). [245] Allenes decorated with electron-withdrawing groups such as allenoesters and allenones 2 have been employed in the organocatalytic asymmetric addition of β-ketoesters 582 (Scheme 99a). [246] The transformation takes place in the presence of chiral quaternary amine 583 as organocatalyst delivering vinyl adducts 584 with very good yields and high enantioselectivity (Scheme 99a).…”

Section: Open-chain Structures From Allenonesmentioning

confidence: 99%

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Highlighting the Rich Chemistry of the Allenone Moiety

Almendros

Alonso

2023

Adv Synth Catal

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Conjugated and non-conjugated allenones appear as recurring motifs in organic synthesis, natural products and mechanistic investigations showing unique properties and applications. The ability of allenones to build cycles has provided a direct access to strained systems, medium-sized rings, arenes, heterocycles and complex polycycles. In addition, allenones have served as models in mechanistic investigations and catalysis. The critic compilation herein presented will provide an exhaustive overview of the synthetic possibilities allenones may offer, which certainly will inspire our community in their search of more efficient synthetic methodologies, preparation of biological and pharmaceutical targets, and improve our knowledge in theoretical organic chemistry. Great part of this review will discuss synthetic aspects, catalysis innovation and mechanistic insights of the chemical transformations implying the allenone motif. In addition, many examples on total synthesis and pharmacologically active compounds will be described. We hope that this overview will be attractive to the organic chemistry, synthetic chemistry, catalysis, theoretical chemistry, natural products and medicinal chemistry communities. 3.5. Synthesis of Spirocycles and Bridged Structures 3.6. Open-Chain Structures from Allenones 3.7. Allenones in Total Synthesis 4.

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Section: Synthetic Utilitymentioning

confidence: 99%

Section: Open-chain Structures From Allenonesmentioning

confidence: 99%

Highlighting the Rich Chemistry of the Allenone Moiety

Almendros

Alonso

2023

Adv Synth Catal

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“…[68][69][70] Therefore, in 2015, Yi et al reported a convenient procedure from both economic and environmental perspective for the hydration of the electron-poor allenic esters/ketones 88 to assemble diverse 1,3-dicarbonyl compounds 89 a-k in the power of oxone/DMF under mild reaction conditions (Scheme 25). [71] The detailed mechanistic routes (route A & route B) for the oxone-mediated hydration of allenic esters and ketones to generate the corresponding keto-derivatives is shown visibly in the Scheme 26.…”

Section: Hydration Of Allene Derivativesmentioning

confidence: 99%

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

2022

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Presently, the major cornerstone of the research community is to develop green as well as sustainable protocols involving inexpensive catalysts and/or reagents without the usage of hazardous solvents under globally friendlier conditions in order to shelter both mankind and environment. Therefore, needless to say, there is always a supreme need to surrogate the older, costlier and unsafe strategies with the novel economically inexpensive and environmental benign ones. To this context, in recent past, oxone® (triple salt), a very cheap oxidizing agent having the chemical formula 2KHSO5 ⋅ KHSO4 ⋅ K2SO4 and enwrapped with the unique characteristics like easy handling, non‐toxic, safe, eco‐friendly, non‐polluting, stable, and nicely soluble in water, in addition to its utility for large‐scale synthesis etc. Bearing the importance of this versatile reagent in mind, we envisioned to update the recent advances made in this direction. Consequently, in this particular review article, the developments made in the arena of oxone chemistry covering from 2013 to 2020 have been revealed as no report appeared in the literature after a wonderful Chem. Rev. published by the group of Hussain in 2013. Herein, a comprehensive detail of a variety of oxidative transformations along with the complete plausible mechanistic steps have been exposed. For sure, present review would be a very helpful tool to the scientific community not only working in the area of organic synthesis but also to the researchers working in other branches of science and technologies as well.

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ChemInform Abstract: Oxone‐Promoted Hydration of Electron‐Deficient Allenic Esters and Ketones into 1,3‐Dicarbonyl Compounds.

Zheng

Nie

et al. 2015

ChemInform

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Oxone-promoted hydration of electron-deficient allenic esters and ketones into 1,3-dicarbonyl compounds

Cited by 4 publications

References 37 publications

Highlighting the Rich Chemistry of the Allenone Moiety

Highlighting the Rich Chemistry of the Allenone Moiety

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

ChemInform Abstract: Oxone‐Promoted Hydration of Electron‐Deficient Allenic Esters and Ketones into 1,3‐Dicarbonyl Compounds.

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