Catalytic atroposelective synthesis of heterobiaryls with vicinal C−C and N−N diaxes via dynamic kinetic resolution

Han, Tian-Jiao; Guan, Chun-Yan; Li, Na; Dong, Rui; Xu, Li-Ping; Xiao, Xiao; Wang, Min-Can; Mei, Guang-Jian

doi:10.1016/j.isci.2023.107978

Cited by 6 publications

(1 citation statement)

References 66 publications

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“…12 Lu and Houk realized asymmetric N–H functionalization by Brønsted base catalysis to access 1-aminopyrroles and 3-amino-quinazolinones (Scheme 1b), 13 and Li and co-workers also reported the synthesis of N–N axially chiral 3-amino-quinazolinones via N -acylation and N -alkylation using the strategy of asymmetric N–H functionalization via asymmetric organocatalysis. 14 Very recently, an N-heterocyclic carbene-catalyzed amidation reaction for the atroposelective synthesis of N–N axially chiral 3-amino quinazolinones was demonstrated by the Biju group. 15 Liu and Lu synthesized 1,1′-bipyrrole atropisomers through the desymmetrization strategy via asymmetric Cu-catalyzed alkylation and arylation reactions.…”

Section: Introductionmentioning

confidence: 99%

Atroposelective synthesis of N–N axially chiral pyrrolyl(aza)-quinolinone by de novo ring formation

Huang,

Li,

Yang

et al. 2024

Org. Chem. Front.

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Section: Introductionmentioning

confidence: 99%

Atroposelective synthesis of N–N axially chiral pyrrolyl(aza)-quinolinone by de novo ring formation

Huang,

Li,

Yang

et al. 2024

Org. Chem. Front.

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Recent Advances in the Reaction of MBH Carbonates: Scope and Mechanism

Shao,

Zhang,

Meng

2024

Asian J Org Chem

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In recent years, Morita‐Baylis‐Hillman (MBH) carbonates have been extensively used in domino reactions for the synthesis of novel heterocyclic or chain compounds. This review aims to highlight the progress made in the last decade in the synthesis of a series of compounds from the uncyclized reaction or annulation of MBH carbonates. Most of the work mentioned in this review strongly demonstrates that MBH carbonates have excellent reaction activity and research value as a representative substrate in the field of organic synthesis. We hope the summary and understanding of the reactivity of MBH carbonates can inspire chemists to apply these substrates in the design of more efficient domino reactions, which may be beneficial for the organic synthesis and drug chemistry.

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Divergent Synthesis of Chiroptical Molecular Switches Based on 1,2-Diaxial Atropisomers

Han,

Yang,

et al. 2024

JACS Au

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The development of chiroptical molecular switches for chiral sensing, data communication, optical displays, chiral logic gates, and asymmetric catalysis is currently a vibrant frontier of science and technology. Herein, we report a practical artificial dynamic system based on a 1,2-diaxial atropisomer. Organocatalytic parallel kinetic resolution allows the divergent synthesis of two sets of stereoisomers with vicinal C–C and N–N axes from the same racemic single-axis substrates. By simply varying the configuration of the single catalyst, all four stereoisomers are accessible. The successive conduction of covalent unlocking/locking and thermal-isomerization processes enables sequential switching between all four atropisomeric states with electronic circular dichroism signal reversal, providing an example of multistate chiroptical molecular switches.

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Catalytic atroposelective synthesis of heterobiaryls with vicinal C−C and N−N diaxes via dynamic kinetic resolution

Cited by 6 publications

References 66 publications

Atroposelective synthesis of N–N axially chiral pyrrolyl(aza)-quinolinone by de novo ring formation

Atroposelective synthesis of N–N axially chiral pyrrolyl(aza)-quinolinone by de novo ring formation

Recent Advances in the Reaction of MBH Carbonates: Scope and Mechanism

Divergent Synthesis of Chiroptical Molecular Switches Based on 1,2-Diaxial Atropisomers

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