Diastereo- and enantioselective synthesis of biaryl aldehydes bearing both axial and central chirality

Huang, Fen; Tao, Ling-Fei; Liu, Jiyong; Qian, Linghui; Liao, Jia‐Yu

doi:10.1039/d3cc00708a

Cited by 12 publications

(4 citation statements)

References 49 publications

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“…In the proposed mechanism (Scheme 27b), the reductive quenching process of the photoexcited 4CzIPN* by Hantzsch ester (HE) led to 4CzIPN *À , which produced Co Nearly at the same time, Qian, Liao, and co-workers developed an Ag/L-catalyzed desymmetric (3 + 2) cycloaddition of prochiral biaryl dialdehydes 1 with activated isocyanides 2 to access a series of biaryl aldehydes 3 bearing a stereogenic CÀ C axis and two adjacent stereogenic carbon centers (Scheme 28). [65]…”

Section: Other Biaryl Atropisomers With C-stereogenic Centersmentioning

confidence: 99%

“…Nearly at the same time, Qian, Liao, and co‐workers developed an Ag/ L ‐catalyzed desymmetric (3+2) cycloaddition of prochiral biaryl dialdehydes 1 with activated isocyanides 2 to access a series of biaryl aldehydes 3 bearing a stereogenic C−C axis and two adjacent stereogenic carbon centers (Scheme 28). [65] …”

Section: Atropisomers With C‐stereogenic Centersmentioning

confidence: 99%

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Catalytic Asymmetric Synthesis of Atropisomers Bearing Multiple Chiral Elements: An Emerging Field

Zhang,

Li,

Liu

et al. 2023

Angew Chem Int Ed

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With the rapid development of asymmetric catalysis, the demand for the enantioselective synthesis of complex and diverse molecules with different chiral elements is increasing. Owing to the unique features of atropisomerism, the catalytic asymmetric synthesis of atropisomers has attracted a considerable interest from the chemical science community. In particular, introducing additional chiral elements, such as carbon center chirality, heteroatomic chirality, planar chirality, and helical chirality, into atropisomers provides an opportunity to incorporate new properties into axially chiral compounds, thus expanding the potential applications of atropisomers. Thus, it is important to perform catalytic asymmetric transformations to synthesize atropisomers bearing multiple chiral elements. In spite of challenges in such transformations, in recent years, chemists have devised powerful strategies under asymmetric organocatalysis or metal catalysis, synthesizing a wide range of enantioenriched atropisomers bearing multiple chiral elements. Therefore, the catalytic asymmetric synthesis of atropisomers bearing multiple chiral elements has become an emerging field. This minireview summarizes the rapid progress in this field and indicates challenges, thereby promoting this field to a new horizon.

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Section: Other Biaryl Atropisomers With C-stereogenic Centersmentioning

confidence: 99%

Section: Atropisomers With C‐stereogenic Centersmentioning

confidence: 99%

Catalytic Asymmetric Synthesis of Atropisomers Bearing Multiple Chiral Elements: An Emerging Field

Zhang,

Li,

Liu

et al. 2023

Angew Chem Int Ed

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“…Asymmetric catalysis with NHCs as chiral catalysts has been a powerful organocatalytic tool to construct complex molecular architectures containing central chirality . It was not until recently that much more attention was paid to the construction of axial chirality, and a series of elegant works were reported to deliver C–C and C–N axially chiral compounds through NHC-catalysis . For example, Zhang and Zheng reported an atroposelective synthesis of axially chiral aldehydes by NHC-catalyzed oxidative esterification via a sequential desymmetrization/kinetic resolution process (Scheme b) .…”

Section: Introductionmentioning

confidence: 99%

Atroposelective Synthesis of Axially Chiral Diaryl Ethers by N-Heterocyclic-Carbene-Catalyzed Sequentially Desymmetric/Kinetic Resolution Process

Li,

Ti,

Miao

et al. 2024

J. Org. Chem.

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We describe herein an N-heterocyclic-carbenecatalyzed atroposelective synthesis of axially chiral diaryl ethers. Through a sequentially enantioselective desymmetric process and a kinetic resolution process, the products could be constructed in good yields with excellent enantiopurities. Both alcohols and phenols were compatible with this catalytic system. The axially chiral carboxylic acids derived from the esters were proven to be potential chiral ligands for asymmetric synthesis, for example, Rh(III)-catalyzed enantioselective C−H functionalization.

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“…Among them, the desymmetrization of prochiral compounds has emerged as an efficient and straightforward approach. Therefore, many classic transformations have been conducted in a desymmetric manner, such as reductive couplings of biaryl dialdehydes, Minisci reaction using α-amino acid esters and 5-arylpyrimidines as the coupling partner, [3 + 2] cycloaddition reaction of biaryl dialdehydes, hydroarylation of vinyl ethers or bicycloalkenes, and intramolecular dehydrogenative C–H silylation to access silicon-central and axial chiralities (Scheme B). Very recently, Li et al reported a Co-catalyzed photoreductive enantioselective desymmetric functionalization of dialdehyde to deliver axially and centrally chiral diaryl ethers …”

mentioning

confidence: 99%

Enantioselective Synthesis of Axially and Centrally Chiral Styrenes via Nickel-Catalyzed Desymmetric Hydrocyanation of Biaryl Dienes

Li,

Cai,

et al. 2024

Org. Lett.

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Herein, a highly regio-, enantio-, and diastereoselective nickel-catalyzed desymmetric hydrocyanation of biaryl dienes for the simultaneous construction of axial and central chiralities is presented, which offers a convenient approach to a variety of tirenes containing the union of an axially chiral biaryl and a centrally α-chiral nitrile under mild conditions using a commercially available catalyst. The synthetic utility is highlighted by the development of a novel axially chiral phosphine ligand and biphenyl-based chiral diene ligand and their potential applications in the field of asymmetric catalytic reactions.

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Diastereo- and enantioselective synthesis of biaryl aldehydes bearing both axial and central chirality

Abstract: We describe herein an intriguing method for the synthesis of biaryl aldehydes bearing both axial and central chirality through a desymmetric [3+2] cycloaddition reaction of activated isocyanides with prochiral biaryl...

Cited by 12 publications

References 49 publications

Catalytic Asymmetric Synthesis of Atropisomers Bearing Multiple Chiral Elements: An Emerging Field

Catalytic Asymmetric Synthesis of Atropisomers Bearing Multiple Chiral Elements: An Emerging Field

Atroposelective Synthesis of Axially Chiral Diaryl Ethers by N-Heterocyclic-Carbene-Catalyzed Sequentially Desymmetric/Kinetic Resolution Process

Enantioselective Synthesis of Axially and Centrally Chiral Styrenes via Nickel-Catalyzed Desymmetric Hydrocyanation of Biaryl Dienes

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