Takeo Kawabata

International University of Health and Welfare

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Kaoru Fuji

International University

103

Takumi Furuta

Kyoto Pharmaceutical University

Y. Ueda

Kyoto University

Takahiro Sasamori

University of Tsukuba

Norihiro Tokitoh

Kyoto University

Kazunori Tsubaki

Kyoto Prefectural University

Tomoyuki Yoshimura

International University of Health and Welfare

Manabu Node

Kyoto Pharmaceutical University

Shohei Hamada

Kanazawa University

Takuya Murai

Kyoto Pharmaceutical University

Cooperative Institutions

Kyoto University

207

Kyoto Bunkyo University

121

Kyoto University Institute for Chemical Research

121

The University of Tokyo

Kyoto Pharmaceutical University

Osaka University

Instituto de Investigaciones Químicas

Tohoku University

University of Science and Technology of China

Tokyo Institute of Technology

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アライン類を用いたα‐アミノ酸誘導体のキラリティ記憶を介したα‐アリール化:四置換炭素を有するベンゾシクロブテノン類の不斉合成

Organic Letters (2017)

Kasamatsu Koji Tomoyuki Yoshimura Attila Mándi Tohru Taniguchi Kenji Monde

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Synthesis of Chiral Dotriacontanaphthalenes: How Many Naphthalene Units Are We Able To Elaborately Connect?

The Journal of Organic Chemistry (2009)

Daisuke Sue Kazuto Takaishi Takunori Harada Reiko Kuroda Takeo Kawabata

(S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S)-dotriacontanaphthalenes 32A-E alternately possessing butoxy and methoxy side chains were precisely constructed through a bottom-up synthesis, and their absolute configurations and fluorescence quantum yields were determined.

10.1021/jo900463t

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Enantioselective preparation of mechanically planar chiral rotaxanes by kinetic resolution strategy

Nature Communications (2021)

Ayumi Imayoshi Bhatraju Vasantha Lakshmi Y. Ueda Tomoyuki Yoshimura Aki Matayoshi

Asymmetric synthesis of mechanically planar chiral rotaxanes and topologically chiral catenanes has been a long-standing challenge in organic synthesis. Recently, an excellent strategy was developed based on diastereomeric synthesis of rotaxanes and catenanes with mechanical chirality followed by removal of the chiral auxiliary. On the other hand, its enantioselective approach has been quite limited. Here, we report enantioselective preparation of mechanically planar chiral rotaxanes by kinetic resolution of the racemates via remote asymmetric acylation of a hydroxy group in the axis component, which provides an unreacted enantiomer in up to >99.9% ee in 29% yield (the theoretical maximum yield of kinetic resolution of racemate is 50%). While the rotaxane molecules are expected to have conformational complexity, our original catalysts enabled to discriminate the mechanical chirality of the rotaxanes efficiently with the selectivity factors in up to 16.

Kinetic resolution

10.1038/s41467-020-20372-0

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ASYMMETRIC INTRAMOLECULAR CONJUGATE ADDITION OF α-AMINO ACID DERIVATIVES VIA RACEMIZATION-FREE EQUILIBRIUM OF INTERMEDIARY CHIRAL ENOLATES

Heterocycles (2012)

Takeo Kawabata Daiki Monguchi Tomoyuki Yoshimura Kazuyuki Irie Kazuhiro Hayashi

A highly enantioselective route to a multi-substituted indoline derivative via intramolecular conjugate addition of an -amino acid derivative has been developed.Enantioselectivity of the reaction was almost independent from the temperature, while the diastereoselectivity was totally dependent on the temperature.High diastereomeric ratios observed at the higher temperatures were assumed to be the results from an equilibrium process between axially chiral enolate intermediates.

Racemization

Conjugate

Diastereomer

Indoline

Derivative (finance)

10.3987/com-12-s(n)129

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Citations (4)

Front Cover: Catalyst‐Dependent Rate‐Determining Steps in Regiodivergent Vinylogous Aza‐Morita‐Baylis‐Hillman Reactions with N‐Ts Imines (Asian J. Org. Chem. 3/2022)

Asian Journal of Organic Chemistry (2022)

Naruhiro Gondo Ryuichi Hyakutake Koki Fujimura Y. Ueda Katsuhiko Nakano

The mechanistic analysis of catalyst-controlled regiodivergent aza-Morita-Baylis-Hillman reactions of vinylcyclopentenone is described. DABCO-catalyzed reaction gives the α-adduct exclusively (red reaction) and DMAP-catalyzed reaction produces the γ-adduct selectively (blue reaction). The analysis revealed that the rate-determining step (RDS) of the DABCO-catalyzed α-selective reactions is the Mannich-type C−C bond formation step, whereas the RDS of the DMAP-catalyzed γ-selective reactions seems to be the β-elimination step. More information can be found in the Full Paper by Yoshihiro Ueda, Masahiro Yamanaka, Takeo Kawabata et al.

DABCO

Baylis–Hillman reaction

10.1002/ajoc.202200033

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Rotaxane Synthesis by an End‐Capping Strategy via Swelling Axle‐Phenols

Angewandte Chemie International Edition (2023)

Koki Fujimura Y. Ueda Yousuke Yamaoka Kiyosei Takasu Takeo Kawabata

A method for rotaxane synthesis by enlargement of the size of the terminal phenol group of the axle component by aromatic bromination has been developed. This method may be regarded as an end-capping strategy involving the swelling of the phenol group at the axle terminal. The advantages of the present strategy include: ready availability of axle components with a variety of swelling precursors, wide product scope (19 examples given including a [3]rotaxane), mild conditions for the swelling process, rich potential for the derivatization of the brominated rotaxanes, and possible release of the axle component by degradative dethreading of the thermally stable brominated rotaxanes under the basic conditions.

Rotaxane

10.1002/anie.202303078

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Citations (3)

CCDC 2069935: Experimental Crystal Structure Determination

The Cambridge Structural Database (2023)

Naruhiro Gondo Koki Fujimura Ryuichi Hyakutake Y. Ueda Takeo Kawabata

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc27gy3s

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Corrigendum to “Second basic pKa: An overlooked parameter in predicting phospholipidosis-inducing potential of diamines” [Bioorg. Med. Chem. Lett. 30 (2020) 126933]

Bioorganic & Medicinal Chemistry Letters (2020)

Hiroki Sakai Hidekazu Inoue Kenji Murata Tetsuya Toba Naohiro Takemoto

Phospholipidosis

10.1016/j.bmcl.2020.127422

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P-197 Development of an Asymmetric Aldol Reaction Based on Memory of Chirality

International Symposium on the Chemistry of Natural Products (2006)

Toshihide Watanabe Takeo Kawabata

Chirality

Aldol reaction

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ChemInform Abstract: Enantioselective Creation of Quaternary Carbon Centers Through Addition‐Elimination Reaction: Asymmetric Nitroolefination of 3‐Substituted 2‐Oxindoles.

ChemInform (1998)

Kaoru Fuji Takeo Kawabata T. OHMORI M. Shang Manabu Node

Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Quaternary carbon

Carbon fibers

10.1002/chin.199827133

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