Application of chiral triazole-substituted iodoarenes in the enantioselective construction of spirooxazolines

Abazid, Ayham H.; Nachtsheim, Boris J.

doi:10.1039/d1cc03246a

Cited by 11 publications

(3 citation statements)

References 51 publications

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“…However, (+)‐ 16 produced the compound 20 in 28 % yield (1 % ee ) and (−)‐ 16 in 31 % yield (5 % ee ), indicating that these compounds are also not selective catalysts. The absolute configuration of the products 18 , [17n,24] 20 , [25] 22 [26] and 24 [27] were assigned using data reported in literature.…”

Section: Resultsmentioning

confidence: 99%

Chiral Iodotriptycenes: Synthesis and Catalytic Applications

2022

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Section: Resultsmentioning

confidence: 99%

Chiral Iodotriptycenes: Synthesis and Catalytic Applications

2022

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“…However, (+)-16 produced the compound 20 in 28 % yield (1 % ee) and (À )-16 in 31 % yield (5 % ee), indicating that these compounds are also not selective catalysts. The absolute configuration of the products 18, [17n,24] 20, [25] 22 [26] and 24 [27] were assigned using data reported in literature.…”

Section: Chemistryopenmentioning

confidence: 99%

Chiral Iodotriptycenes: Synthesis and Catalytic Applications

2022

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Invited for this month′s cover picture is the group of Thomas Wirth at Cardiff University (UK). The cover picture shows two structures of triptycenes. In each of these molecules all three aromatic rings are different with the rigid structure of the molecules making them chiral. The two sp3‐carbons shown in red and green are the stereocentres with defined configuration. These molecules contain the crucial iodine functionality which are utilised to generate hypervalent iodine(III)‐catalysts in situ. The authors acknowledge Dr. Yu Wang for the creation of the cover image. Read the full text of their Research Article at 10.1002/open.202200145.

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“…Nevertheless, most of these reactions still rely on either intramolecular manner or intermolecular transformations of functionalized starting materials. [2][3][4][5][6][7] These processes use -substituted -naphthols (R ≠ H) bearing substituents at the  position to prevent unwanted side reactions. The oxidation coupling, -position functionalization, or [3+2]-cycloaddition reactions of -unsubstituted -naphthols are favorable pathways as their aromatic properties still been maintained.…”

Section: Introductionmentioning

confidence: 99%

Dearomatization of α-Unsubstituted β-Naphthols

Xu,

Li,

Feng

et al. 2023

Synlett

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This Account summarizes the highly appealing dearomatization reactions of β-naphthols for the synthesis of highly functionalized, three-dimensional structures starting with simple planar aromatic compounds. The reactions are categorized mainly from the viewpoint of the construction of carbon–hydrogen, carbon–carbon, and carbon–hetero bonds (C–N/O, C–Cl, C–F) at the α-position of β-naphthols. The dearomatized products play an important role in organic synthesis and materials science.1 Introduction2 Construction of Carbon–Hydrogen Bonds at the α-Position of β-Naphthols3 Construction of Carbon–Carbon Bonds at the α-Position of β-Naphthols4 Construction of Carbon–Nitrogen/Oxygen Double Bond at the α-Position of β-Naphthols5 Construction of Carbon–Carbon and Carbon–Oxygen Bonds at the α-Position of β-Naphthols6 Construction of Carbon–Halogen Bonds at the α-Position of β-Naphthols7 Conclusion

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Application of chiral triazole-substituted iodoarenes in the enantioselective construction of spirooxazolines

Abstract: A catalytic highly enantioselective synthesis of spirooxazolines is presented. Starting from readily available 2-naphthol-substituted benzamides and using catalytic amounts of a chiral triazole-substituted iodoarene catalyst, a variety of spirooxazolines can...

Cited by 11 publications

References 51 publications

Chiral Iodotriptycenes: Synthesis and Catalytic Applications

Chiral Iodotriptycenes: Synthesis and Catalytic Applications

Chiral Iodotriptycenes: Synthesis and Catalytic Applications

Dearomatization of α-Unsubstituted β-Naphthols

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