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Atroposelective Synthesis of Novel Axially Chiral Molecules
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Atroposelective Synthesis of Novel Axially Chiral Molecules

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (29 February 2024) | Viewed by 15562

Special Issue Editors

Prof. Dr. Ying He

E-Mail Website
Guest Editor
School of Chemistry and Chemical Engineering, Nanjing University of Science & Technology, Nanjing 210094, China
Interests: axially chiral chemistry; asymmetric synthesis; asymmetric allylic substitution; stereospecific isomerization; chirality transfer
Dr. Xinxin Shao

E-Mail Website
Guest Editor
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 310036, Zhejiang, China
Interests: amination; fluorine chemistry; reductive coupling; C-S bond formation; radicals

Special Issue Information

Dear Colleagues,

In recent years, axially chiral molecules have attracted the interests of researchers since they play a significant role not only in the field of asymmetric synthesis, but in the occurrence of biologically active molecules. This Special Issue mainly focuses on the atroposelective synthesis of axially chiral molecules and their applications.

Prof. Dr. Ying He
Dr. Xinxin Shao
Guest Editors

Manuscript Submission Information

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Keywords

  • axially chiral molecules
  • atroposelective synthesis
  • asymmetric catalysis
  • axially chiral ligands
  • axially chiral catalysts

Published Papers (7 papers)

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Research

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13 pages, 2333 KiB  
Article
Atroposelective Amination of Indoles via Chiral Center Induced Chiral Axis Formation
by Yong Wang, Jingxue Yan, Yiqing Jiang, Zexuan Wei, Zhenlin Tu, Chao Dong, Tao Lu, Yadong Chen and Jie Feng
Molecules 2022, 27(24), 9008; https://doi.org/10.3390/molecules27249008 - 17 Dec 2022
Cited by 1 | Viewed by 1529
Abstract
The construction of an N–C chiral axis for N-aryl indole derivatives is meaningful as they widely exist in functionalized molecules. This work provides a novel method for this purpose via amination of amino acid derivatives at the C2 position of the indole and [...] Read more.
The construction of an N–C chiral axis for N-aryl indole derivatives is meaningful as they widely exist in functionalized molecules. This work provides a novel method for this purpose via amination of amino acid derivatives at the C2 position of the indole and chiral center induced chiral axis formation. The protocol of this transformation is easily accessible, not requiring metal or an organic chiral catalyst, endowing this method with great potential in the construction of axis chiral N-aryl indoles. Full article
(This article belongs to the Special Issue Atroposelective Synthesis of Novel Axially Chiral Molecules)
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Scheme 1

8 pages, 1024 KiB  
Communication
DBU Promoted Polysubstituted Arene Formation via a Michael Addition/Cyclization/Elimination Cascade Reaction
by Guishun Bai, Yang Yang, Xingyue Wang, Jiamin Wu, Hong Wang, Xinyi Ye and Xiaoze Bao
Molecules 2022, 27(23), 8167; https://doi.org/10.3390/molecules27238167 - 23 Nov 2022
Cited by 1 | Viewed by 1237
Abstract
The straightforward construction of polysubstituted arenes is essential in both synthetic chemistry and medicinal chemistry. Herein, we reported a DBU promoted Michael addition/cyclization/elimination cascade reaction between vinylogous malononitrile derivatives and chlorinated nitrostyrenes for the synthesis of polysubstituted arenes. The method features mild reaction [...] Read more.
The straightforward construction of polysubstituted arenes is essential in both synthetic chemistry and medicinal chemistry. Herein, we reported a DBU promoted Michael addition/cyclization/elimination cascade reaction between vinylogous malononitrile derivatives and chlorinated nitrostyrenes for the synthesis of polysubstituted arenes. The method features mild reaction conditions, wide substrate scope and high yield. Interestingly, preliminary study of the enantioselective version of this cascade was conducted to give chiral biaryl atropisomers with up to 40% ee through center-to-axial chirality transfer strategy. Full article
(This article belongs to the Special Issue Atroposelective Synthesis of Novel Axially Chiral Molecules)
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22 pages, 2555 KiB  
Article
Catalytic Enantioselective Synthesis of N-C Axially Chiral N-(2,6-Disubstituted-phenyl)sulfonamides through Chiral Pd-Catalyzed N-Allylation
by Sota Fukasawa, Tatsuya Toyoda, Ryohei Kasahara, Chisato Nakamura, Yuuki Kikuchi, Akiko Hori, Gary J. Richards and Osamu Kitagawa
Molecules 2022, 27(22), 7819; https://doi.org/10.3390/molecules27227819 - 13 Nov 2022
Cited by 2 | Viewed by 1409
Abstract
Recently, catalytic enantioselective syntheses of N-C axially chiral compounds have been reported by many groups. Most N-C axially chiral compounds prepared through a catalytic asymmetric reaction possess carboxamide or nitrogen-containing aromatic heterocycle skeletons. On the other hand, although N-C axially chiral sulfonamide derivatives [...] Read more.
Recently, catalytic enantioselective syntheses of N-C axially chiral compounds have been reported by many groups. Most N-C axially chiral compounds prepared through a catalytic asymmetric reaction possess carboxamide or nitrogen-containing aromatic heterocycle skeletons. On the other hand, although N-C axially chiral sulfonamide derivatives are known, their catalytic enantioselective synthesis is relatively underexplored. We found that the reaction (Tsuji–Trost allylation) of allyl acetate with secondary sulfonamides bearing a 2-arylethynyl-6-methylphenyl group on the nitrogen atom proceeds with good enantioselectivity (up to 92% ee) in the presence of (S,S)-Trost ligand-(allyl-PdCl)2 catalyst, affording rotationally stable N-C axially chiral N-allylated sulfonamides. Furthermore, the absolute stereochemistry of the major enantiomer was determined by X-ray single crystal structural analysis and the origin of the enantioselectivity was considered. Full article
(This article belongs to the Special Issue Atroposelective Synthesis of Novel Axially Chiral Molecules)
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Review

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26 pages, 7991 KiB  
Review
Enantioselective Synthesis of Atropisomers by Oxidative Aromatization with Central-to-Axial Conversion of Chirality
by Clément Lemaitre, Stefania Perulli, Ophélie Quinonero, Cyril Bressy, Jean Rodriguez, Thierry Constantieux, Olga García Mancheño and Xavier Bugaut
Molecules 2023, 28(7), 3142; https://doi.org/10.3390/molecules28073142 - 31 Mar 2023
Cited by 7 | Viewed by 2051
Abstract
Atropisomers are fascinating objects of study by themselves for chemists but also find applications in various sub-fields of applied chemistry. Obtaining them in enantiopure form is far from being a solved challenge, and the past decades has seen a surge of methodological developments [...] Read more.
Atropisomers are fascinating objects of study by themselves for chemists but also find applications in various sub-fields of applied chemistry. Obtaining them in enantiopure form is far from being a solved challenge, and the past decades has seen a surge of methodological developments in that direction. Among these strategies, oxidative aromatization with central-to-axial conversion of chirality has gained increasing popularity. It consists of the oxidation of a cyclic non-aromatic precursors into the corresponding aromatic atropisomers. This review proposes a critical analysis of this research field by delineating it and discussing its historical background and its present state of the art to draw potential future development directions. Full article
(This article belongs to the Special Issue Atroposelective Synthesis of Novel Axially Chiral Molecules)
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Graphical abstract

21 pages, 6272 KiB  
Review
Advances in the Asymmetric Synthesis of BINOL Derivatives
by Everton Machado da Silva, Hérika Danielle Almeida Vidal, Marcelo Augusto Pereira Januário and Arlene Gonçalves Corrêa
Molecules 2023, 28(1), 12; https://doi.org/10.3390/molecules28010012 - 20 Dec 2022
Cited by 9 | Viewed by 3484
Abstract
BINOL derivatives have shown relevant biological activities and are important chiral ligands and catalysts. Due to these properties, their asymmetric synthesis has attracted the interest of the scientific community. In this work, we present an overview of the most efficient methods to obtain [...] Read more.
BINOL derivatives have shown relevant biological activities and are important chiral ligands and catalysts. Due to these properties, their asymmetric synthesis has attracted the interest of the scientific community. In this work, we present an overview of the most efficient methods to obtain chiral BINOLs, highlighting the use of metal complexes and organocatalysts as well as kinetic resolution. Further derivatizations of BINOLs are also discussed. Full article
(This article belongs to the Special Issue Atroposelective Synthesis of Novel Axially Chiral Molecules)
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37 pages, 28381 KiB  
Review
Advances in Atroposelectively De Novo Synthesis of Axially Chiral Heterobiaryl Scaffolds
by Xiaoke Zhang, Ya-Zhou Liu, Huawu Shao and Xiaofeng Ma
Molecules 2022, 27(23), 8517; https://doi.org/10.3390/molecules27238517 - 03 Dec 2022
Cited by 6 | Viewed by 2183
Abstract
Axially chiral heterobiaryl frameworks are privileged structures in many natural products, pharmaceutically active molecules, and chiral ligands. Therefore, a variety of approaches for constructing these skeletons have been developed. Among them, de novo synthesis, due to its highly convergent and superior atom economy, [...] Read more.
Axially chiral heterobiaryl frameworks are privileged structures in many natural products, pharmaceutically active molecules, and chiral ligands. Therefore, a variety of approaches for constructing these skeletons have been developed. Among them, de novo synthesis, due to its highly convergent and superior atom economy, serves as a promising strategy to access these challenging scaffolds including C-N, C-C, and N-N chiral axes. So far, several elegant reviews on the synthesis of axially chiral heterobiaryl skeletons have been disclosed, however, atroposelective construction of the heterobiaryl subunits by de novo synthesis was rarely covered. Herein, we summarized the recent advances in the catalytic asymmetric synthesis of the axially chiral heterobiaryl scaffold via de novo synthetic strategies. The related mechanism, scope, and applications were also included. Full article
(This article belongs to the Special Issue Atroposelective Synthesis of Novel Axially Chiral Molecules)
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Figure 1

57 pages, 24187 KiB  
Review
Construction of Non-Biaryl Atropisomeric Amide Scaffolds Bearing a C–N Axis via Enantioselective Catalysis
by Xiao Xiao, Biao Chen, Yi-Ping Yao, Hai-Jie Zhou, Xu Wang, Neng-Zhong Wang and Fen-Er Chen
Molecules 2022, 27(19), 6583; https://doi.org/10.3390/molecules27196583 - 04 Oct 2022
Cited by 13 | Viewed by 2629
Abstract
The significant scaffold offered by atropisomeric amides with a C–N chiral axis has been extensively utilized for pharmaceuticals, agricultural science, and organic syntheses. As a result, the field of atropisomer synthesis has attracted considerable interest within chemistry communities. To date, a range of [...] Read more.
The significant scaffold offered by atropisomeric amides with a C–N chiral axis has been extensively utilized for pharmaceuticals, agricultural science, and organic syntheses. As a result, the field of atropisomer synthesis has attracted considerable interest within chemistry communities. To date, a range of catalytic atroposelective approaches has been reported for the efficient construction of these challenging scaffolds. However, greatly concise and highly useful methodologies for the synthesis of these atropisomeric compounds, focusing on transition-metal, chiral amine, and phosphoric acid catalysis reactions, etc., are still desirable. Hence, it is indispensable to succinctly and systematically present all such reports by means of disclosing the mechanistic analysis and application, as well as the challenges and issues associated with the establishment of these atropisomers. In this review, we summarize the development of catalytic asymmetric synthetic strategies to access non-biaryl atropisomers rotating around a C–N chiral axis, including the reaction methods, mechanism, late-stage transformations, and applications. Full article
(This article belongs to the Special Issue Atroposelective Synthesis of Novel Axially Chiral Molecules)
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