Enantioselective Control of Both Helical and Axial Stereogenic Elements though an Organocatalytic Approach

Jia, Shiqi; Li, Shan; Liu, Yidong; Qin, Wenling; Yan, Hailong

doi:10.1002/ange.201909214

Cited by 31 publications

(5 citation statements)

References 115 publications

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“…reported the highly enantioselective catalytic synthesis of carbo[6]helicenes through similar sequential alkyne annulations of achiral diynes catalyzed by chiral Au‐complexes. Later, Yan et al [22] . developed an elegant approach to control both the helical and axial chirality of binaphthyl‐containing [6]helicenes during the enantio‐ and diastereoselective stepwise alkyne annulations of achiral diynes catalyzed by chiral basic organocatalysts [23]…”

Section: Resultsmentioning

confidence: 99%

Stereospecific Synthesis of Enantiopure [6]Helicene Containing a Seven‐Membered Ring and [7]Helicene by Acid‐Promoted Stepwise Alkyne Annulations of Doubly Axial‐Chiral Precursors**

et al. 2023

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Enantiopure [6]helicene containing an embedded seven‐membered ring and carbo[7]helicene (>99 % ee) with opposite helicity were simultaneously and quantitatively (>99 %) synthesized with a perfect stereospecificity through stepwise acid‐promoted intramolecular alkyne annulations of doubly axial‐chiral cyclization precursors. The helical handedness of the [6]‐ and [7]helicenes was fully stereocontrolled by the doubly axial chirality of the precursors as a result of complete axial‐to‐helical chirality transfer. The cyclizations proceeded in a stepwise manner; the first six‐membered ring formation was followed by the kinetically controlled seven‐ or six‐membered ring formation with or without helix‐inversion of a [4]helicene intermediate generated during the first cyclization step, thus quantitatively producing enantiopure circularly polarized luminescent [6]‐ and [7]helicenes with opposite helicity.

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Section: Resultsmentioning

confidence: 99%

Stereospecific Synthesis of Enantiopure [6]Helicene Containing a Seven‐Membered Ring and [7]Helicene by Acid‐Promoted Stepwise Alkyne Annulations of Doubly Axial‐Chiral Precursors**

et al. 2023

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“…We can conclude that transition‐metal‐catalyzed [2+2+2] cycloaddition of alkynes, click reaction of azides with alkynes, and the organocatalyzed intermolecular [3+2], [4+2], and [8+2] cycloadditions of alkynes provide numerous possibilities for the synthesis of axially chiral compounds. Furthermore, the intramolecular cyclization of alkynylnaphthol or alkynylaniline derivatives has made significant contributions to the development of indole‐based axially chiral heterobiaryls with C−C or C−N axis, many interesting works using VQM intermediates have been reported by Yan and other groups, various chiral molecules with multiple‐stereogenic elements [43] and chiral helicenes [14e,85] were prepared efficiently. On the other hand, many name reactions, such as Paal–Knorr, Friedländer, Cacchi, Barton–Zard, and the Attanasi reaction have become useful tools to construct atropisomeric heterobiaryls via transition‐metal‐ and organo‐catalyzed intermolecular cyclization.…”

Section: Discussionmentioning

confidence: 99%

Atroposelective Synthesis of Heterobiaryls through Ring Formation

Sun

Sharif

Chen

et al. 2023

Chemistry A European J

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Atropisomeric heterobiaryls play a vital role in natural products, chiral ligands, organocatalysts, and other research fields, which have aroused great interest from chemists in recent years. Until now, a growing number of optically active heterobiaryls based on indole, quinoline, isoquinoline, pyridine, pyrrole, azole, and benzofuran skeletons have been successfully synthesized through metal or organic catalytic cross-coupling, functionalization of prochiral or racemic heterobiaryls, and ring formation. Among different strategies for the atroposelective synthesis of heterobiaryls, the strategy of ring formation has become a vital tool toward this goal. In this review, we summarize the enantioselective synthesis of axially chiral heterobiaryls through ring formation approaches, such as cycloaddition, cyclization, and chirality conversion. Meanwhile, the reaction mechanism and the corresponding applications of the chiral heterobiaryls are also discussed.[a] H.

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“…The editable and complex structures of proteins make them attractive to a wide range of functions and applications beyond biochemistry. [ 1–9 ] In recent decades, significant strides have been made in adopting versatile proteins/peptides and amino acids to design materials with diverse morphologies, dimensions, and functions. [ 10–14 ]…”

Section: Introductionmentioning

confidence: 99%

Versatile Protein and Its Subunit Biomolecules for Advanced Rechargeable Batteries

Liu

2023

Advanced Materials

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Rechargeable batteries are of great significance for alleviating the growing energy crisis by providing efficient and sustainable energy storage solution. However, the multiple issues associated with the diverse components in a battery system as well as the interphase problems greatly hinder their applications. Proteins and its subunits, peptides and amino acids, are versatile biomolecules. Functional groups in different amino acids endow these biomolecules with unique properties including the self‐assembly, ion conducting, antioxidation, great affinity to exterior species, etc. Besides, protein and its subunit materials can not only work in solid forms, but also in liquid forms when dissolved in solutions, making them more versatile to realize materials engineering via diverse approaches. In this review, we aim to offer a comprehensive understanding about the properties of proteins and its subunits, and research progress of using these versatile biomolecules to address the engineering issues of various rechargeable batteries, including alkali‐ion batteries, lithium‐sulfur batteries, metal‐air batteries, and flow batteries. The state‐of‐the‐art advances in electrode, electrolyte, separator, binder, catalyst, interphase modification, as well as recycle of rechargeable batteries are involved, and the impacts of biomolecules on electrochemical properties are particularly emphasized. Finally, perspectives on this interesting field are also provided.This article is protected by copyright. All rights reserved

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Enantioselective Control of Both Helical and Axial Stereogenic Elements though an Organocatalytic Approach

Cited by 31 publications

References 115 publications

Stereospecific Synthesis of Enantiopure [6]Helicene Containing a Seven‐Membered Ring and [7]Helicene by Acid‐Promoted Stepwise Alkyne Annulations of Doubly Axial‐Chiral Precursors**

Stereospecific Synthesis of Enantiopure [6]Helicene Containing a Seven‐Membered Ring and [7]Helicene by Acid‐Promoted Stepwise Alkyne Annulations of Doubly Axial‐Chiral Precursors**

Atroposelective Synthesis of Heterobiaryls through Ring Formation

Versatile Protein and Its Subunit Biomolecules for Advanced Rechargeable Batteries

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