Article
Chemistry, Medicinal
Takuya Murai, Shohei Hamada, Yusuke Kobayashi, Takahiro Sasamori, Takumi Furuta
Summary: The preparation, optical resolution, and structural investigations of a series of axially chiral biaryl dicarboxylic acids bearing oxygen, sulfur, and selenium atoms were conducted. The study revealed that the conformational control of these compounds can be achieved through chalcogen bonding interactions and tetrel bonding interactions. The physical and chiroptical properties of these biaryl dicarboxylic acids were also explored.
CHEMICAL & PHARMACEUTICAL BULLETIN
(2022)
Article
Chemistry, Multidisciplinary
Liwen Wei, Jiaomeng Li, Yi Zhao, Qinglong Zhou, Zhikang Wei, Yuhang Chen, Xinglong Zhang, Xing Yang
Summary: The development of catalytic asymmetric reactions using water as a reactant is challenging due to the low nucleophilicity and small size of water, which leads to reactivity and stereoselectivity control issues. In this study, we demonstrate a chiral phosphoric acid (CPA) catalyzed ring-opening reaction of biaryl oxazepines with water, achieving high enantioselectivity. The success of this reaction is attributed to the use of a new SPINOL-derived CPA catalyst and the high reactivity of biaryl oxazepine substrates towards water under acidic conditions. Density functional theory calculations suggest that the reaction proceeds via a dynamic kinetic resolution pathway, with the CPA catalyzed addition of water to the imine group being both enantio- and rate-determining.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Nasir Tajuddeen, Doris Feineis, Heiko Ihmels, Gerhard Bringmann
Summary: The naphthylisoquinoline (NIQ) alkaloids are a class of natural biaryls with diverse structures, biosynthetic pathways, and pharmacological properties. The synthesis of these compounds is challenging, with the stereocontrolled construction of the biaryl bond as a key step. This review focuses on the synthesis of NIQs with a stable biaryl axis, emphasizing the preparation of atropisomers. Internal and external asymmetric inductions, as well as innovative approaches, are discussed in detail.
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Article
Chemistry, Physical
Ashish Sharma, Stavros Athanasopoulos, Elango Kumarasamy, Chanakarn Phansa, Amir Asadpoordarvish, Randy P. Sabatini, Raj Pandya, Kaia R. Parenti, Samuel N. Sanders, Dane R. McCamey, Luis M. Campos, Akshay Rao, Murad J. Y. Tayebjee, Girish Lakhwani
Summary: By designing a compound containing an axially chiral binaphthyl bridge and utilizing its chiroptical response as a marker for intra-molecular singlet fission chromophore-bridge-chromophore interactions, the study demonstrates the promising application of chiroptical techniques in investigating these interactions.
JOURNAL OF PHYSICAL CHEMISTRY A
(2021)
Article
Biochemistry & Molecular Biology
Shoma Hirokawa, Nagao Kobayashi, Soji Shimizu
Summary: The study elaborates inherently chiral subporphyrins by forming a fused pyran ring at the periphery, showing that the chiroptical properties can be controlled by peripheral substitution and meso-aryl substituents. The circular dichroism (CD) properties of chiral subporphyrins are largely affected by the peripheral substituents and the dihedral angles between the meso-aryl substituents and the subporphyrin core.
Article
Physics, Multidisciplinary
Dongsheng Song, Rafal E. Dunin-Borkowski
Summary: This study presents a method for three-dimensional magnetic measurement at atomic scale using EMCD technology, which allows for obtaining signals related to magnetization in three Cartesian directions by using a subangstrom convergent electron beam in STEM. Atomic resolution EMCD signals from all three directions can be separately acquired by moving the detector, and signal enhancement can be achieved by using a defocused electron beam.
PHYSICAL REVIEW LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Ming Wu, Yi-Wei Chen, Qian Lu, Yong-Bin Wang, Jun Kee Cheng, Peiyuan Yu, Bin Tan
Summary: A highly efficient method for the synthesis of atropisomers through functionalization of the Si-C bond between dinaphthosiloles and silanol nucleophiles was presented. The versatile nature of the Si-C bond allows for the facile derivatization of chiral products into other functional atropisomers.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Ming Wu, Yi-Wei Chen, Qian Lu, Yong-Bin Wang, Jun Kee Cheng, Peiyuan Yu, Bin Tan
Summary: Chiral organosilanes are important chemical entities in the development of functional organic materials, asymmetric catalysis, and medicinal chemistry. An efficient method for atroposelective synthesis of biaryl siloxane atropisomers via organocatalytic Si-C bond functionalization of dinaphthosiloles with silanol nucleophiles is presented. The reaction proceeds through an asymmetric protonation and simultaneous Si-C bond cleavage/silanolysis sequence in the presence of a newly developed chiral Bronsted acid catalyst. The versatile nature of the Si-C bond expands the applicability of this method.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Materials Science, Multidisciplinary
Wouter Heyvaert, Adrian Pedrazo-Tardajos, Ajinkya Kadu, Nathalie Claes, Guillermo Gonzalez-Rubio, Luis M. Liz-Marzan, Wiebke Albrecht, Sara Bals
Summary: Chirality in inorganic nanoparticles and nanostructures has attracted increasing scientific interest due to their ability to interact differently with circularly polarized light. Quantifying the degree of chirality in objects of nanoscale is challenging, but the authors introduce a methodology based on helical geometrical properties to quantify the helicity of complex chiral nanomaterials. They demonstrate that analyzing individual particles can provide significant insights into the origin of chiroptical properties.
ACS MATERIALS LETTERS
(2022)
Article
Materials Science, Multidisciplinary
Herman Duim, Maria Antonietta Loi
Summary: This article discusses the potential of chiral hybrid organic-inorganic metal halides (HMHs) in the field of optics, examining the impact of chiral transfer on electronic structure and optical properties. It further explores efforts to improve and tune the chiroptical response, while also proposing future research directions for enhancing chiral HMHs.
Article
Chemistry, Multidisciplinary
Zeyu Feng, Chenlu He, Yifan Xie, Chutian Zhang, Jiahe Li, Dingdong Liu, Zifan Jiang, Xin Chen, Gang Zou
Summary: Chiral metal nanostructures have recently gained attention due to their strong chiroptical properties and enhanced light-matter interactions. In this study, twisted-stacked silver nanowire arrays (TNAs) with independently controllable CD signals at interband transition and plasmonic extinction regions were constructed. These TNAs exhibited high sensitivity towards protein secondary structures, with different responses depending on the protein's beta-sheets or alpha-helices content. The mutually independent optical activities at the interband transition and plasmonic extinction regions complemented each other, providing enhanced sensitivity and reliability in chiral biosensing.
Article
Chemistry, Organic
Tohru Taniguchi
Summary: This article describes the use of vibrational circular dichroism spectroscopy to study the stereochemistry of carbodiimides and allenes, and discusses a strategy to obtain carbodiimides with one-handed chirality by using conformationally restrained frameworks.
Article
Chemistry, Multidisciplinary
Liang Yan, Manoj K. Jana, Peter C. Sercel, David B. Mitzi, Wei You
Summary: The study presents a new type of 2D hybrid perovskites with a unique combination of chirality and alkyl-aryl functionality, determined by noncovalent intermolecular interactions in their crystal structures. The mixed-cation perovskites exhibit a circular dichroism distinct from purely chiral cation analogues, providing a new avenue for tuning the chiroptical properties of known chiral perovskites. Mixing chiral cations with achiral cations may offer a potential way to tailor the spin-based properties in 2D hybrid perovskites.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Mengjia Cen, Jiawei Wang, Jianxun Liu, Huilin He, Ke Li, Wenfeng Cai, Tun Cao, Yan Jun Liu
Summary: A new type of self-aligned suspended chiral bilayer metasurface is demonstrated, which can exhibit significant optical chirality and label-free discrimination of chiral molecules at zeptomole level, with higher sensitivity compared to conventional circular dichroism spectroscopy.
ADVANCED MATERIALS
(2022)
Article
Chemistry, Multidisciplinary
Jinyi Dong, Yihao Zhou, Jiahao Pan, Chao Zhou, Qiangbin Wang
Summary: In this study, gold nanobipyramids (AuNBPs) were assembled into static and dynamic chiral plasmonic nanostructures using DNA origami. Compared to conventional chiral dimers of gold nanorods (AuNRs), AuNBP dimers exhibited more intriguing chiroptical responses, suggesting they could be a superior alternative for constructing chiral plasmonic nanostructures for biosensing.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Petra Schmitz, Marcus Malter, Gregor Lorscheider, Christina Schreiner, Aude Carboni, Sabine Choppin, Francoise Colobert, Andreas Speicher
Article
Chemistry, Multidisciplinary
Daniel Meidlinger, Lisa Marx, Catalina Bordeianu, Sabine Choppin, Francoise Colobert, Andreas Speicher
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Organic
Andreas Speicher, Matthias Groh, Markus Hennrich, Anh-Minh Huynh
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2010)
Article
Chemistry, Organic
Anu Schaumloeffel, Matthias Groh, Michael Knauer, Andreas Speicher, Gerhard Bringmann
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2012)
Article
Chemistry, Organic
Matthias Groh, Daniel Meidlinger, Gerhard Bringmann, Andreas Speicher
Article
Multidisciplinary Sciences
Linjun Zhang, Jie Xi, Guoqing Xu, Hua Shu, Xiaoyi Wang, Ping Li
Article
Multidisciplinary Sciences
Li Zhang, Wenqiang Chang, Bin Sun, Matthias Groh, Andreas Speicher, Hongxiang Lou
Article
Chemistry, Organic
Andreas Speicher, Judith Holz
TETRAHEDRON LETTERS
(2010)
Article
Chemistry, Organic
Lisa Dejon, Andreas Speicher
TETRAHEDRON LETTERS
(2013)
Article
Chemistry, Inorganic & Nuclear
Gerhard Bringmann, Dominik Hager, Anu Schaumloeffel, Matthias Groh, Andreas Speicher
TETRAHEDRON-ASYMMETRY
(2013)
Article
Biochemistry & Molecular Biology
Lisa Dejon, Hamdoon Mohammed, Peng Du, Claus Jacob, Andreas Speicher
Article
Chemistry, Organic
Lisa Marx, Daniel Lamberty, Sabine Choppin, Francoise Colobert, Andreas Speicher
Summary: This study presents an atroposelective macrocyclization process using an oxidative Heck system to achieve the first atropo-enantiopure synthesis of isoriccardin C, which demonstrates a new strategy for synthesizing biologically active optical isomers.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Laura Stief, Andreas Speicher
Summary: A polyprenyl side chain was introduced into the heterocyclic quinoline moiety through Suzuki-Miyaura coupling, enabling the synthesis of Aurachin B from Stigmatella aurantiaca. This prenylated quinoline could then be transformed into the related compound Aurachin A through an epoxidation-ring opening cascade.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Medicinal
Andreas Speicher, Judith Holz, Alexandra Hoffmann
NATURAL PRODUCT COMMUNICATIONS
(2011)
