Cr-catalyzed chiral allenone synthesis<i>via</i>sequential radical–polar crossover and Oppenauer oxidation

Zeng, Xianrong; Zhang, Fenghua; Wang, Zhaobin

doi:10.1039/d2qo01676a

Cited by 9 publications

(3 citation statements)

References 68 publications

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“…[69] In a recent report, bromobutynes 83 b have been employed in chromium-catalyzed addition to aldehydes to generate the corresponding allenols, which in situ undergo Oppenauer oxidation to yield the expected allenones 2 (Scheme 15c). [70] Chiral ligand L5 has provided enantiomeric excess of up to 95% (Scheme 15c). [70]…”

Section: One-pot Methodologiesmentioning

confidence: 99%

“…The TA−Au‐catalyzed addition of phenylacetylene to enantioenriched (96% ee) propargyl alcohol 83 a has formed optically active (91% ee) β‐allenone 85 a as one example of efficient chirality transfer (Scheme 15b) [69] . In a recent report, bromobutynes 83 b have been employed in chromium‐catalyzed addition to aldehydes to generate the corresponding allenols, which in situ undergo Oppenauer oxidation to yield the expected allenones 2 (Scheme 15c) [70] . Chiral ligand L5 has provided enantiomeric excess of up to 95% (Scheme 15c) [70] …”

Section: Synthesis Of 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: One-pot Methodologiesmentioning

confidence: 99%

Section: Synthesis Of Allenonesmentioning

confidence: 99%

Highlighting the Rich Chemistry of the Allenone Moiety

Almendros

Alonso

2023

Adv Synth Catal

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“…Coverage is focused on intermolecular couplings of unactivated alcohols or aldehydes (no directing groups or vicinal dicarbonyl compounds). The large body of literature on metal-catalyzed alkene hydroacylation, and other C–H activation-initiated processes that convert alcohols or aldehydes to ketones, which often require chelating/directing groups, has been extensively reviewed and is not surveyed. , Multicomponent processes (for example, 2:1 couplings of allenes with aldehydes to form ketones) and those involving ring formation or ring cleavage are not covered, nor are stepwise processes in which C–C bond formation and alcohol oxidation are mechanistically uncoupled …”

Section: Introduction and Scope Of Reviewmentioning

confidence: 99%

Intermolecular Metal-Catalyzed C–C Coupling of Unactivated Alcohols or Aldehydes for Convergent Ketone Construction beyond Premetalated Reagents

et al. 2023

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Intermolecular metal-catalyzed C−C couplings of unactivated primary alcohols or aldehydes to form ketones are catalogued. Reactions are classified on the basis of pronucleophile. Protocols involving premetalated reagents or reactants that incorporate directing groups are not covered. These methods represent an emerging alternative to classical multistep protocols for ketone construction that exploit premetalated reagents and/or steps devoted to redox manipulations and carboxylic acid derivatization.

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Chromium‐Catalyzed Reductive Cross‐Coupling to Construct C−SS Bonds from Unactivated Alkyl Electrophiles

Zhang,

Wang,

et al. 2024

ChemCatChem

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Low‐valent chromium catalysts are cheap and less toxic compared to other transition metal catalysts. Here in, we reported a ligand‐free chromium(III)‐catalyzed manganese reductive cross‐coupling of unactivated alkyl electrophiles, such as alkyl sulfonates and alkyl chlorides, with trisulfide dioxides as thiolation agents to form carbon‐sulfur bonds. The powerful method featured ample substrate scope and wide functional group tolerance, constructing a large number of unsymmetrical disulfides under simple conditions.

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Cr-catalyzed chiral allenone synthesisviasequential radical–polar crossover and Oppenauer oxidation

Abstract: The Nozaki-Hiyama-Kishi (NHK) reaction is a powerful and reliable tool in chiral alcohol synthesis and finds broad application in the total synthesis of biologically important molecules. However, chiral ketone synthesis...

Cited by 9 publications

References 68 publications

Highlighting the Rich Chemistry of the Allenone Moiety

Highlighting the Rich Chemistry of the Allenone Moiety

Intermolecular Metal-Catalyzed C–C Coupling of Unactivated Alcohols or Aldehydes for Convergent Ketone Construction beyond Premetalated Reagents

Chromium‐Catalyzed Reductive Cross‐Coupling to Construct C−SS Bonds from Unactivated Alkyl Electrophiles

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