The Direct Conversion of Esters to Ketones Enabled by a Traceless Activating Group

Fier, Patrick S.; Roberts, Riley; Larson, Reed T.

doi:10.1021/acs.orglett.3c00992

Cited by 3 publications

(2 citation statements)

References 32 publications

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“…More significantly, 3a may be hydrolyzed to produce axial chiral carboxylic acid, which has special qualities for enantioselective catalysis and almost no enantiopurity degradation. A single-step method for the conversion of esters 3a to ketones 7 in 85% yield and 94% ee …”

Section: Results and Discussionmentioning

confidence: 99%

Carbene-Catalyzed Atroposelective Construction of Chiral Diaryl Ethers

Liu,

Yuan,

Dai

et al. 2024

J. Org. Chem.

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Atropoisomeric chemotypes of diaryl ethers-related scaffolds are prevalent in naturally active compounds. Nevertheless, there remains considerable research to be carried out on the catalytic asymmetric synthesis of these axially chiral molecules. In this instance, we disclose an N-heterocyclic carbene (NHC)-catalyzed synthesis of axially chiral diaryl ethers via atroposelective esterification of dialdehyde-containing diaryl ethers. NHC desymmetrization produces axially chiral diaryl ether atropisomers with high yields and enantioselectivities in moderate circumstances. Chiral diaryl ether compounds may be precursors for highly functionalized diaryl ethers with bioactivity and chiral ligands for asymmetric catalysis.

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Section: Results and Discussionmentioning

confidence: 99%

Carbene-Catalyzed Atroposelective Construction of Chiral Diaryl Ethers

Liu,

Yuan,

Dai

et al. 2024

J. Org. Chem.

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“…A single-step method for the conversion of esters 3a to ketones 7 in 85 % yield and 94 % ee. [23] Aiming to develop novel axially chiral ligands/catalysts, the selective derivatization of alcohol 8 was carried out, and hydrolysis of 8 afforded product 9. Compound 8 (99% ee, after recrystallization with Et2O/hexane) was selected as the ligand for the Iridium/Brønsted acid cooperative catalyzed asymmetric allylic substitution reactions.…”

Section: Resultsmentioning

confidence: 99%

Carbene-Catalyzed Atroposelective Construction of Chiral Diaryl Ethers

Liu,

Yuan,

Dai

et al. 2023

Preprint

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Atropoisomeric chemotypes of diaryl ethers related scaffolds are prevalent in naturally active compounds. Nevertheless, there remains considerable research to be carried out on the catalytic asymmetric synthesis of these axially chiral molecules. In this instance, we disclose the first N-heterocyclic carbene catalyzed synthesis of axially chiral diaryl ethers via atroposelective esterification of dialdehyde-containing diaryl ethers. The reaction proceeds mathematically through a desymmetrization method catalyzed by NHC, which results in the production of axially chiral diaryl ether atropisomers with good yields and high enantioselectivities in mild conditions. The chiral diaryl ether compounds can be utilized as precursors for further transformation into highly functionalized diaryl ethers with potential bioactivity and as chiral ligands with uses in asymmetric catalysis.

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Total Synthesis of Lucidumone: Attempted Shortcuts, Dead Ends and Lessons Learnt

de la Torre,

Huang,

Laporte

et al. 2023

Synthesis

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Lucidumone is a meroterpenoid isolated from the mushroom Ganoderma lucidum, displaying selective COX-2 inhibitory activity. In this work, we detail our synthetic efforts which led to the first enantioselective synthesis of lucidumone in 13 steps (longest linear sequence). Beyond the key retro-[4+2]/intramolecular Diels–Alder cascade, we discuss the difficulties regarding fragment assembly, introduction of the methyl ketone moiety and choice of adequate protecting group.

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The Direct Conversion of Esters to Ketones Enabled by a Traceless Activating Group

Cited by 3 publications

References 32 publications

Carbene-Catalyzed Atroposelective Construction of Chiral Diaryl Ethers

Carbene-Catalyzed Atroposelective Construction of Chiral Diaryl Ethers

Carbene-Catalyzed Atroposelective Construction of Chiral Diaryl Ethers

Total Synthesis of Lucidumone: Attempted Shortcuts, Dead Ends and Lessons Learnt

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