Synthesis of quinol-type heterobiaryls<i>via</i>an acid-catalyzed heteroannulation of alkynes and<i>o</i>-aminobenzaldehydes

Jian, Qing-Song; Gou, Bo-Bo; Wang, Shaojie; Sun, Huai‐Ri; Sharif, Atif; Wang, Yongqiang; Zhou, Ling; Chen, Jie

doi:10.1039/d2qo01813f

Cited by 3 publications

(2 citation statements)

References 63 publications

(15 reference statements)

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“…The reaction is compatible with up to 37 substrates with excellent yields and enantioselectivities, and the resulting atropisomeric C2-arylquinoline skeletons can be converted into multiple functional axially chiral molecules while preserving good ee values. Notably, CPA-catalyzed heteroannulation of alkynyl naphthanols and aminobenzaldehydes gave only racemic heterobiaryls due to a lower rotation barrier of OH group [45]. In terms of the construction and application of axially chiral quinoline derivatives, Jiang et al tend to make them into new N,P ligands.…”

Section: Chiral Phosphoric Acids (Cpas)mentioning

confidence: 99%

Asymmetric Synthesis of Axially Chiral Molecules via Organocatalytic Cycloaddition and Cyclization Reactions

et al. 2023

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Atropisomeric molecules are present in many natural products, biologically active compounds, chiral ligands and catalysts. Many elegant methodologies have been developed to access axially chiral molecules. Among them, organocatalytic cycloaddition and cyclization have attracted much attention because they have been widely used in the asymmetric synthesis of biaryl/heterobiaryls atropisomers via construction of carbo- and hetero-cycles. This strategy has undoubtedly become and will continue to be a hot topic in the field of asymmetric synthesis and catalysis. This review aims to highlight the recent advancements in this field of atropisomer synthesis by using different organocatalysts in cycloaddition and cyclization strategies. The construction of each atropisomer, its possible mechanism, the role of catalysts, and its potential applications are illustrated.

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Section: Chiral Phosphoric Acids (Cpas)mentioning

confidence: 99%

Asymmetric Synthesis of Axially Chiral Molecules via Organocatalytic Cycloaddition and Cyclization Reactions

et al. 2023

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“…Different with the π complexation model in transition-metal-catalyzed reactions with alkynes, noncovalent interaction with substituted alkynes is a common activation model in organocatalysis. The addition of active electrophiles such as protons and halogens to the alkynes in the aid of organic bases or acids would first generate ortho -quinone methides, , followed by intermolecular/intramolecular addition of the other nucleophiles to complete the reaction (Scheme a). Organocatalysts play a key role during these processes by employing dual hydrogen bond activation modes with the hydroxyl group and electrophiles.…”

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confidence: 99%

Aromatic Amine and Chiral Phosphoric Acid Synergistic Catalyzed Cascade Reaction of Alkynylnaphthols with Aldehydes

Wang,

Meng,

Tang

et al. 2024

Org. Lett.

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A novel approach using aromatic amines and chiral phosphoric acids in a synergistic catalytic cascade reaction of 2alkynylnaphthols with aldehydes has been established. This method offers a direct route to preparing flavanone analogues with excellent stereoselectivity. Mechanistic studies reveal a sequential process involving addition, elimination, cyclization, and hydrolysis in which aromatic amines and chiral phosphoric acids play key roles via imineenamine and hydrogen bonding models.

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Chiral Brønsted Acid‐Catalyzed Asymmetric Reaction via Vinylidene Ortho‐Quinone Methides

Zhu,

Yang,

2024

Chemistry A European J

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Vinylidene ortho‐quinone methides (VQMs) have been proven to be versatile and crucial intermediates in the catalytic asymmetric reaction in last decade, and thus have drawn considerable concentrations on account of the practical application in the construction of enantiomerically pure functional organic molecules. However, in comparison to the well established chiral Brønsted base‐catalyzed asymmetric reaction via VQMs, chiral Brønsted acid‐catalyzed reaction is rarely studied and there is no systematic summary to date. In this review, we summarize the recent advances in the chiral Brønsted acid‐catalyzed asymmetric reaction via VQMs according to three types of reactions: a) intermolecular asymmetric nucleophilic addition to VQMs; b) intermolecular asymmetric cycloaddition of VQMs; c) intramolecular asymmetric cyclization of VQMs. Finally, we put forward the remained challenges and opportunities for potential breakthroughs in this area.

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Synthesis of quinol-type heterobiarylsviaan acid-catalyzed heteroannulation of alkynes ando-aminobenzaldehydes

Abstract: Herein, we report a practical strategy for the synthesis of structurally novel quinol-type heterobiaryls. A wide range of 1-(quinolin-2-yl)naphthalen-2-ols were afforded with good to excellent yields under mild reaction conditions....

Cited by 3 publications

References 63 publications

Asymmetric Synthesis of Axially Chiral Molecules via Organocatalytic Cycloaddition and Cyclization Reactions

Asymmetric Synthesis of Axially Chiral Molecules via Organocatalytic Cycloaddition and Cyclization Reactions

Aromatic Amine and Chiral Phosphoric Acid Synergistic Catalyzed Cascade Reaction of Alkynylnaphthols with Aldehydes

Chiral Brønsted Acid‐Catalyzed Asymmetric Reaction via Vinylidene Ortho‐Quinone Methides

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