Recent advances in stereoselective construction of fluorinated quaternary carbon centers from fluorinated compounds

Li, Zongwei; Fan, Lin; Liu, Guodu

doi:10.1039/d4ob00457d

Org. Biomol. Chem.

2024

DOI: 10.1039/d4ob00457d

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Recent advances in stereoselective construction of fluorinated quaternary carbon centers from fluorinated compounds

Zongwei Li,

Lin Fan,

Guodu Liu

Abstract: There are many fluorinated quaternary carbon structural units in pharmaceuticals and bioactive compounds. Organic chemists are interested in the stereoselective synthesis of fluorinated quaternary carbon structural units. Constructing a fluorinated...

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Cited by 2 publications

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Base‐Promoted Diastereoselective Addition of 2‐Aryloxy‐2‐Fluoroketones to N‐(tert‐Butylsulfinyl)Imines

Wang,

Wei,

Jin

et al. 2024

ChemistrySelect

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The asymmetric construction of a quaternary fluorine‐containing stereogenic carboncenter is highly valuable for the development of fluoroine‐containing bioactive molecules. Herein, a base‐promoted, diastereoselective Mannich‐type reaction of 2‐aryloxy‐2‐fluoroketones with N‐(tert‐butylsulfinyl)imines has been developed. A number of the addition products featuring a fluorinated quaternary stereocarbon centre and a β‐fluoroamine structural motif have been readily obtained in good yields with moderate to good diastereoselectivities. The absolute configuration of the major diasteromer was determined by X‐ray crystallography analysis, and a closed transition‐state mode was proposed to explain the stereochemical outcome of this reaction. In addition, the addition product was efficiently converted into a α‑fluoro‐β‐amino alcohol through desulfinylation followed by reduction of the carbonyl group.

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Base‐Promoted Diastereoselective Addition of 2‐Aryloxy‐2‐Fluoroketones to N‐(tert‐Butylsulfinyl)Imines

Wang,

Wei,

Jin

et al. 2024

ChemistrySelect

View full text Add to dashboard Cite

show abstract

Copper-Catalyzed Asymmetric Tertiary Radical Cyanation for the Synthesis of Chiral Tetrasubstituted Monofluoroacyl Nitriles

Liu,

Jiang,

Tang

et al. 2024

Org. Lett.

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Recent advances in stereoselective construction of fluorinated quaternary carbon centers from fluorinated compounds

Abstract: There are many fluorinated quaternary carbon structural units in pharmaceuticals and bioactive compounds. Organic chemists are interested in the stereoselective synthesis of fluorinated quaternary carbon structural units. Constructing a fluorinated...

Cited by 2 publications

References 65 publications

Base‐Promoted Diastereoselective Addition of 2‐Aryloxy‐2‐Fluoroketones to N‐(tert‐Butylsulfinyl)Imines

Base‐Promoted Diastereoselective Addition of 2‐Aryloxy‐2‐Fluoroketones to N‐(tert‐Butylsulfinyl)Imines

Copper-Catalyzed Asymmetric Tertiary Radical Cyanation for the Synthesis of Chiral Tetrasubstituted Monofluoroacyl Nitriles

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