Non-central chirality in organic chemistry

• Ken Tanaka and
• Naohiko Yoshikai

Beilstein J. Org. Chem. 2026, 22, 370–371, doi:10.3762/bjoc.22.24

• ; chiroptical properties; molecular chirality; Chirality is a foundational concept in organic chemistry, traditionally framed around tetrahedral carbon stereocenters. Over the past decades, however, it has become increasingly clear that molecular handedness is not confined to localized points in space. Axes

Chiral phosphoric acid-catalyzed asymmetric synthesis of helically chiral, planarly chiral and inherently chiral molecules

• Wei Liu and
• Xiaoyu Yang

Beilstein J. Org. Chem. 2025, 21, 1864–1889, doi:10.3762/bjoc.21.145

• .21.145 Abstract Chiral molecules, distinguished by nonsuperimposability with their mirror image, play crucial roles across diverse research fields. Molecular chirality is conventionally categorized into the following types: central chirality, axial chirality, planar chirality and helical chirality, along

• molecular chirality has been investigated comparatively less. This Review provides a comprehensive overview of the recent emerging advancements in asymmetric synthesis of planarly chiral, helically chiral and inherently chiral molecules using CPA catalysis, while offering insights into future developments

• pharmaceutical, agrochemical and asymmetric synthesis as well as materials science, to name a few examples. Molecular chirality is typically classified into four types of chiral elements: central (point) chirality, axial chirality, planar chirality and helical chirality (Figure 2). Moreover, unique forms of

Unique halogen–π association detected in single crystals of C–N atropisomeric N-(2-halophenyl)quinolin-2-one derivatives and the thione analogue

• Mai Uchibori,
• Nanami Murate,
• Kanako Shima,
• Tatsunori Sakagami,
• Ko Kanehisa,
• Gary James Richards,
• Akiko Hori and
• Osamu Kitagawa

Beilstein J. Org. Chem. 2025, 21, 1748–1756, doi:10.3762/bjoc.21.138

• , ought to have different halogen bonding properties, and should be explored as different chemical entities. Meanwhile, there are very few studies on halogen bonding related to molecular chirality such as those shown in Figure 1 [27][28][29][30]. In addition, the studies on the comparison of

Pd-Catalyzed asymmetric allylic amination with isatin using a P,olefin-type chiral ligand with C–N bond axial chirality

• Natsume Akimoto,
• Kaho Takaya,
• Yoshio Kasashima,
• Kohei Watanabe,
• Yasushi Yoshida and
• Takashi Mino

Beilstein J. Org. Chem. 2025, 21, 1018–1023, doi:10.3762/bjoc.21.83

• Education, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan Molecular Chirality Research Center, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan Soft Molecular Activation Research Center, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan Institute for

Asymmetric synthesis of β-amino cyanoesters with contiguous tetrasubstituted carbon centers by halogen-bonding catalysis with chiral halonium salt

• Yasushi Yoshida,
• Maho Aono,
• Takashi Mino and
• Masami Sakamoto

Beilstein J. Org. Chem. 2025, 21, 547–555, doi:10.3762/bjoc.21.43

• Yasushi Yoshida Maho Aono Takashi Mino Masami Sakamoto Institute for Advanced Academic Research (IAAR), Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan Molecular Chirality Research Center, Graduate School of Engineering, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba-shi

One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na₂S₂O₈

• Teppei Sasaki,
• Katsuhiko Moriyama and
• Hideo Togo

Beilstein J. Org. Chem. 2018, 14, 345–353, doi:10.3762/bjoc.14.22

• Teppei Sasaki Katsuhiko Moriyama Hideo Togo Department of Chemistry, Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan Molecular Chirality Research Center, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan 10.3762/bjoc.14.22 Abstract

Remarkable functions of sn-3 hydroxy and phosphocholine groups in 1,2-diacyl-sn-glycerolipids to induce clockwise (+)-helicity around the 1,2-diacyl moiety: Evidence from conformation analysis by ¹H NMR spectroscopy

• Yoshihiro Nishida,
• Mengfei Yuan,
• Kazuo Fukuda,
• Kaito Fujisawa,
• Hirofumi Dohi and
• Hirotaka Uzawa

Beilstein J. Org. Chem. 2017, 13, 1999–2009, doi:10.3762/bjoc.13.196

• Yoshihiro Nishida Mengfei Yuan Kazuo Fukuda Kaito Fujisawa Hirofumi Dohi Hirotaka Uzawa Nanobiology Course in Graduate School of Advanced Integration Science & Molecular Chirality Research Center, Chiba University, Matsudo 271-8510, Chiba, Japan Nanomaterials Research Institute, National Institute

• chiral biomolecules have an asymmetric sn-glycerol backbone. Although sn-glycerol is symmetric, an sn-3 phosphate group makes it chiral with an (R)-configuration at the sn-2 position [4]. Such molecular chirality is crucial to not only their biological activities but also for their metaphysical

• -glycerols [18], indicating that the disparity between gt(+) and gg(−) conformers varies widely by influences from sn-3 groups. Helical properties constitute one of the major factors in determining the molecular chirality [20] of not only proteins and nucleic acids but also simpler biomolecules [17][18][19

Determination of the absolute stereostructure of a cyclic azobenzene from the crystal structure of the precursor containing a heavy element

• Reji Thomas and
• Nobuyuki Tamaoki

Beilstein J. Org. Chem. 2016, 12, 2211–2215, doi:10.3762/bjoc.12.212

• pharmaceutical ingredients [11]. In addition to the special interest in molecular chirality in diverse fields of biology and pharmaceutical chemistry, several chiral molecules have been synthesised and studied for their stereostructure-dependent physical properties such as optical activity [12][13][14][15][16

Unusual polymorphism in new bent-shaped liquid crystals based on biphenyl as a central molecular core

• Anna Kovářová,
• Svatopluk Světlík,
• Václav Kozmík,
• Jiří Svoboda,
• Vladimíra Novotná,
• Damian Pociecha,
• Ewa Gorecka and
• Natalia Podoliak

Beilstein J. Org. Chem. 2014, 10, 794–807, doi:10.3762/bjoc.10.75

• cyano end-capped bent-shaped materials it was documented [29][30][31] that reversing the position of hydroxylic and carboxylic groups exerts a profound effect on the mesophase properties. The bent-shaped molecules can create polar mesophases in spite of lack of molecular chirality. The most frequently

The interplay of configuration and conformation in helical perylenequinones: Insights from chirality induction in liquid crystals and calculations

• Elisa Frezza,
• Silvia Pieraccini,
• Stefania Mazzini,
• Alberta Ferrarini and
• Gian Piero Spada

Beilstein J. Org. Chem. 2012, 8, 155–163, doi:10.3762/bjoc.8.16

• configuration of the dopant: Enantiomers induce oppositely handed cholesterics. Only in the last few decades has the generation of cholesteric liquid crystals and the amplification of the molecular chirality observed upon doping nematic phases with chiral derivatives attracted great interest in the field of

[3.3]Dithia-bridged cyclophanes featuring a thienothiophene ring: synthesis, structures and conformational analysis

• Sabir H. Mashraqui,
• Yogesh Sanghvikar,
• Shailesh Ghadhigaonkar,
• Sukeerthi Kumar,
• Auke Meetsma and
• Elise Trân Huu Dâu

Beilstein J. Org. Chem. 2009, 5, No. 74, doi:10.3762/bjoc.5.74

• °C with an estimated conformational energy barrier of >100 kJ mol−1 [27]. The presence of substituents on the thienothiophene ring (as well as on the phenyl ring in 11) and the absence of conformational inversion endow these with molecular chirality rendering them potentially resolvable. Temperature

Chiral amplification in a cyanobiphenyl nematic liquid crystal doped with helicene-like derivatives

• Alberta Ferrarini,
• Silvia Pieraccini,
• Stefano Masiero and
• Gian Piero Spada

Beilstein J. Org. Chem. 2009, 5, No. 50, doi:10.3762/bjoc.5.50

• Abstract The addition of a chiral non-racemic dopant to a nematic liquid crystal (LC) has the effect of transferring the molecular chirality to the phase organization and a chiral nematic phase is formed. This molecular chirality amplification in the LC provides a unique possibility for investigating the

• dopant to a nematic liquid crystal has the effect of transferring the molecular chirality to the phase organization and a chiral nematic (or cholesteric) phase is formed, in which the director rotates perpendicularly to an axis in a helical way (see Figure 1) [1]. For a given nematic host, the handedness

• general review on CD, see refs [22][23]). From a more fundamental point of view, the molecular chirality amplification in LC gives a unique possibility for investigating the relationship between molecular structure, intermolecular interactions, and mesoscale organization. The phenomenon of cholesteric