Recent advances in the cyclization of para-quinone methides

Liu, Xianping; Ren, Yining; Zhu, Longzhi; Li, Tao; Xu, Weifeng; Liu, Yu; Tang, Ke-Wen; Xiong, Biquan

doi:10.1016/j.tet.2023.133655

“…In recent years, the synthetic utilities of p -quinone methides ( p -QMs) have been widely explored. 10 Our group was also involved in the synthesis of various triarylmethanes, 11 carbocycles 12 and heterocycles 13 using p -QMs as synthons. Herein, we report a transition-metal and base-free HMPA-mediated oxygenative carbocyclization of 2-alkynylated p -QMs 14 to access substituted indenones ( d , Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

A HMPA–H₂O mediated oxygenative carbocyclization of 2-alkynylphenyl-substituted p-quinone methides to indenones

Fatma,

Ahmad,

Pankhade

et al. 2024

Org. Biomol. Chem.

0

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Catalytic Asymmetric Synthesis of Inherently Chiral Eight‐Membered O‐Heterocycles through Cross‐[4+4] Cycloaddition of Quinone Methides

Xu,

Zhou,

Liu

et al. 2024

Angewandte Chemie

0

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Inherently chiral eight‐membered rings embedded in tetraphenylene derivatives and hetero‐analogues exhibit unique properties and allow diverse applications. A conceptually viable and straightforward approach to these frameworks is [4+4] cycloaddition, which still remains elusive. In this study, we describe the stereoselective cross‐[4+4] cycloaddition of quinone methides (QMs), leading to the formation of oxa‐analogues of tetraphenylene with exceptional chemo‐, diastereo‐, and enantioselectivity. The structures of these novel rigid eight‐membered O‐heterocycles were explored via single‐crystal X‐ray diffraction and their stereochemical stability was elaborated through both density functional theory (DFT) calculations and thermal racemization experiments. The developed methodology exhibited broad substrate scope and the resulting cross‐[4+4] cycloadducts could be readily transformed into valuable chiral building blocks. Our findings expanded the inherently chiral library of medium‐sized rings and also contributed to the advancement of asymmetric cross‐[4+4] cycloadditions of quinone methides.

show abstract

Catalytic Asymmetric Synthesis of Inherently Chiral Eight‐Membered O‐Heterocycles through Cross‐[4+4] Cycloaddition of Quinone Methides

Xu,

Zhou,

Liu

et al. 2024

Angew Chem Int Ed

0

View full text Add to dashboard Cite

Inherently chiral eight‐membered rings embedded in tetraphenylene derivatives and hetero‐analogues exhibit unique properties and allow diverse applications. A conceptually viable and straightforward approach to these frameworks is [4+4] cycloaddition, which still remains elusive. In this study, we describe the stereoselective cross‐[4+4] cycloaddition of quinone methides (QMs), leading to the formation of oxa‐analogues of tetraphenylene with exceptional chemo‐, diastereo‐, and enantioselectivity. The structures of these novel rigid eight‐membered O‐heterocycles were explored via single‐crystal X‐ray diffraction and their stereochemical stability was elaborated through both density functional theory (DFT) calculations and thermal racemization experiments. The developed methodology exhibited broad substrate scope and the resulting cross‐[4+4] cycloadducts could be readily transformed into valuable chiral building blocks. Our findings expanded the inherently chiral library of medium‐sized rings and also contributed to the advancement of asymmetric cross‐[4+4] cycloadditions of quinone methides.

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Recent advances in the cyclization of para-quinone methides

Cited by 13 publications

References 72 publications

A HMPA–H₂O mediated oxygenative carbocyclization of 2-alkynylphenyl-substituted p-quinone methides to indenones

A HMPA–H₂O mediated oxygenative carbocyclization of 2-alkynylphenyl-substituted p-quinone methides to indenones

Catalytic Asymmetric Synthesis of Inherently Chiral Eight‐Membered O‐Heterocycles through Cross‐[4+4] Cycloaddition of Quinone Methides

Catalytic Asymmetric Synthesis of Inherently Chiral Eight‐Membered O‐Heterocycles through Cross‐[4+4] Cycloaddition of Quinone Methides

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Recent advances in the cyclization of para-quinone methides

Cited by 13 publications

References 72 publications

A HMPA–H2O mediated oxygenative carbocyclization of 2-alkynylphenyl-substituted p-quinone methides to indenones

A HMPA–H2O mediated oxygenative carbocyclization of 2-alkynylphenyl-substituted p-quinone methides to indenones

Catalytic Asymmetric Synthesis of Inherently Chiral Eight‐Membered O‐Heterocycles through Cross‐[4+4] Cycloaddition of Quinone Methides

Catalytic Asymmetric Synthesis of Inherently Chiral Eight‐Membered O‐Heterocycles through Cross‐[4+4] Cycloaddition of Quinone Methides

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Resources

About

A HMPA–H₂O mediated oxygenative carbocyclization of 2-alkynylphenyl-substituted p-quinone methides to indenones

A HMPA–H₂O mediated oxygenative carbocyclization of 2-alkynylphenyl-substituted p-quinone methides to indenones