Primary activation of<i>para</i>-quinone methides by chiral phosphoric acid for enantioselective construction of tetraarylmethanes

Han, Zhengyu; Zhu, Biao; Zang, Yu; Zhang, Chaoshen; Dong, Xiu-Qin; Huang, Hai; Sun, Jianwei

doi:10.1039/d3sc05014a

Chem. Sci.

2024

DOI: 10.1039/d3sc05014a

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Primary activation ofpara-quinone methides by chiral phosphoric acid for enantioselective construction of tetraarylmethanes

Zhengyu Han,

Biao Zhu,

Yu Zang

et al.

Abstract: Demonstrated here is an asymmetric nucleophilic addition via primary activation of para-quinone methides (p-QMs) based on a chiral phosphoric acid catalytic system.

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Manganese‐Mediated Cascade Radical Oxidative Cyclization/1,6‐Conjugate Addition of Unsaturated Oximes with p‐Quinone Methides: Facile Access to β,β‐Diarylmethine Substituted Isoxazolines

Vara,

Thete,

Ghotekar

et al. 2024

Chemistry An Asian Journal

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A simple and efficient strategy for the synthesis of structurally diverse β,β‐diarylmethine substituted isoxazoline derivatives have been developed. This approach employs a manganese‐promoted oxidative cyclization coupled with a 1,6‐conjugate addition of unsaturated oximes to p‐quinone methides. The key features of this study include the formation of C‐O and C‐C bonds through intramolecular and intermolecular interactions, facilitated by in situ generated iminoxyl radicals. β,β‐diarylmethine substituted isoxazolines, bearing a wide range of functional groups, were isolated in high yields

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Manganese‐Mediated Cascade Radical Oxidative Cyclization/1,6‐Conjugate Addition of Unsaturated Oximes with p‐Quinone Methides: Facile Access to β,β‐Diarylmethine Substituted Isoxazolines

Vara,

Thete,

Ghotekar

et al. 2024

Chemistry An Asian Journal

View full text Add to dashboard Cite

show abstract

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Primary activation ofpara-quinone methides by chiral phosphoric acid for enantioselective construction of tetraarylmethanes

Abstract: Demonstrated here is an asymmetric nucleophilic addition via primary activation of para-quinone methides (p-QMs) based on a chiral phosphoric acid catalytic system.

Cited by 1 publication

References 66 publications

Manganese‐Mediated Cascade Radical Oxidative Cyclization/1,6‐Conjugate Addition of Unsaturated Oximes with p‐Quinone Methides: Facile Access to β,β‐Diarylmethine Substituted Isoxazolines

Manganese‐Mediated Cascade Radical Oxidative Cyclization/1,6‐Conjugate Addition of Unsaturated Oximes with p‐Quinone Methides: Facile Access to β,β‐Diarylmethine Substituted Isoxazolines

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