Article
Chemistry, Multidisciplinary
Stuart C. D. Kennington, Saul F. Teloxa, Miguel Mellado-Hidalgo, Oriol Galeote, Sabrina Puddu, Marina Bellido, Pedro Romea, Felix Urpi, Gabriel Aullon, Merce Font-Bardia
Summary: A direct and asymmetric aldol reaction of N-acyl thiazinanethiones with aromatic aldehydes catalyzed by chiral nickel(II) complexes was reported. The reaction gives high yields of O-TIPS-protected anti-aldol adducts with remarkable stereocontrol and atom economy. The removal of the achiral scaffold provides enantiomerically pure intermediates with synthetic interest for producing anti-alpha-amino-beta-hydroxy and alpha,beta-dihydroxy carboxylic derivatives, with theoretical calculations explaining the observed high stereocontrol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Teng Yuan, Kelton Radefeld, Chuan Shan, Carter Wegner, Erin Nichols, Xiaohan Ye, Qi Tang, Lukasz Wojtas, Xiaodong Shi
Summary: Here, we have reported an intermolecular asymmetric hydrative aldol reaction by using a vinyl-gold intermediate under ambient conditions. This reaction provides a base-free approach to β-hydroxy amides with high efficiency, yielding up to 95% and with over 50 examples. The use of vinyl gold intermediate as a reactive nucleophile and Fe(acac)(3) as a critical co-catalyst prevents undesired protodeauration, allowing the transformation to proceed under mild conditions with excellent functional group tolerance and stereoselectivity (>20:1 d.r. and up to 99% ee).
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Organic
Zorana Ferjancic, Radomir N. Saicic
Summary: The combination of organocatalytic aldol reaction and reductive amination allows for rapid, stereoselective synthesis of N-heterocycles, which is of great significance for the synthesis of iminosugars and other polyhydroxylated alkaloids.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Lianqian Wu, Zhihan Zhang, Dunqi Wu, Fei Wang, Pinhong Chen, Zhenyang Lin, Guosheng Liu
Summary: An unprecedented highly enantioselective radical azidation of acrylamides catalyzed by 1 mol% of a copper catalyst is reported. The use of a specific ligand is crucial for generating a monomeric Cu-II azide species for this highly enantioselective transformation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Wen-Wen Zhang, Qiang Wang, Su-Zhen Zhang, Chao Zheng, Shu-Li You
Summary: Satoh-Miura reaction is an important method for extending pi-systems via C-H activation and alkynyl annulation. However, achieving high enantioselectivity remains challenging. In this study, an asymmetric Satoh-Miura reaction using a SCpRh-catalyst is reported, and it is found that choosing the counteranion of the catalyst is crucial for the desired reactivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Nanoscience & Nanotechnology
Miguel Sanchez-Fuente, Alberto Lopez-Magano, Alicia Moya, Ruben Mas-Balleste
Summary: Condensation of BINAPO-(PhCHO)(2) and 1,3,5-tris(4-aminophenyl)benzene(TAPB) leads to a new imine-based chiral organic material (COM) that can be post-functionalized through reductive transformation of imine linkers to amines. Although the imine-based material is not stable enough to be used as a heterogeneous catalyst, the reduced amine-linked framework can be efficiently utilized in asymmetric allylation of various aromatic aldehydes. The obtained yields and enantiomeric excesses are comparable to those observed for the molecular BINAP oxide catalyst, with the added advantage of recyclability offered by the amine-based material.
ACS APPLIED MATERIALS & INTERFACES
(2023)
Article
Chemistry, Organic
Isaac G. Sonsona, Andrea Vicenzi, Marco Guidotti, Giorgiana Denisa Bisag, Mariafrancesca Fochi, Raquel P. Herrera, Luca Bernardi
Summary: The study demonstrates the improved selectivity of an asymmetric aldol reaction by replacing part of the catalyst, and identifies the most suitable reaction conditions. However, these conditions seem to be limited to oxindoles bearing a 3-substituent of funapide.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Jacob Werth, Matthew S. Sigman
Summary: The study utilizes multivariate linear regression analysis to investigate different categories of BOX catalyzed reactions, developing predictive models for various asymmetric catalytic reactions including Cu, Ni, Fe, Mg, and Pd complexes, and reveals the structural requirements necessary for high selectivity through analysis of diverse organometallic intermediates.
Article
Chemistry, Multidisciplinary
Yulin Han, Anni Qin, Qian Zhang, Xue Zhang, Hui Qian, Shengming Ma
Summary: The Rh-catalyzed reaction allows for the efficient synthesis of cis-fused bicyclic products with excellent selectivity and tolerance towards synthetically useful functional groups. The proposed mechanism involves the rapid racemization of the allene moiety in the starting materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Liangliang Zhang, Martin Oestreich
Summary: The passage describes a reaction sequence involving enantioselective copper-catalyzed conjugate silylation and diastereotopic group-selective aldol cyclization. The intramolecular aldol reaction's diastereoselectivity depends on the silicon nucleophile used, and the more basic zinc reagent enables thermodynamically driven cis-to-trans isomerization. A wide range of electron-withdrawing groups, including electron-deficient heterocycles, are compatible with the different procedures developed.
Review
Chemistry, Multidisciplinary
Jia-Qi Xie, Ren-Xiao Liang, Yi-Xia Jia
Summary: This review focuses on recent development of catalytic asymmetric Heck reaction and reductive Heck reaction, covering intermolecular and intramolecular versions since 2011. The article is organized in terms of the catalysts and olefin substrates, providing a clear structure for readers.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Saul F. Teloxa, Miguel Mellado-Hidalgo, Stuart C. D. Kennington, Pedro Romea, Felix Urpi, Gabriel Aullon, Merce Font-Bardia
Summary: A direct and asymmetric aldol reaction between N-azidoacetyl-1,3-thiazolidine-2-thione and aromatic aldehydes catalyzed by a chiral nickel(II)-Tol-BINAP complex has been developed. The reaction gives anti alpha-azido-beta-silyloxy adducts with excellent stereocontrol and high yields. The removal of thiazolidinethione allows for the synthesis of a wide array of enantiomerically pure derivatives, providing a new route to di- and tripeptide blocks containing a beta-aryl-beta-hydroxy-alpha-amino acid.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Eleonora Grandi, Michele Crotti, Marie-Catherine Sigmund, Guangcai Xu, Pieter G. G. Tepper, Gerrit J. J. Poelarends
Summary: Multi-enzymatic cascades using engineered enzymes are a useful tool for synthesizing complex molecules from simple starting materials. In this study, we engineered the enzyme 4-oxalocrotonate tautomerase (4-OT) to have increased aldolase activity. We then used the evolved 4-OT variant in a one-pot two-step cascade to synthesize enantioenriched epoxides from biomass-derived materials with high yields and enantioselectivity. We also developed a three-step enzymatic cascade for the production of chiral aromatic triols with high enantiopurity and good isolated yields.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Applied
Satoshi Sakai, Akane Fujioka, Koji Imai, Kei Uchiyama, Yohei Shimizu, Kosuke Higashida, Masaya Sawamura
Summary: The silver-catalyzed asymmetric aldol reaction of isocyanoacetic acid derivatives with aldehydes has been developed using a chiral prolinol-phosphine ligand as a hydrogen-bond-donating P,N,O ligand. DFT calculations revealed a stepwise reaction mechanism, involving C-C bond formation and subsequent enantioselectivity-determining ring formation. The prolinol moiety of the ligand activates the aldehyde through a two-point hydrogen bond, facilitating the stereocontrolled cyclization. Additional nonclassical hydrogen bonds and London dispersion interactions may also contribute to stereocontrol.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Xing Yang, Pankaj Kumar Majhi, Huifang Chai, Bin Liu, Jun Sun, Ting Liu, Yonggui Liu, Liejin Zhou, Jun Xu, Jiawei Liu, Dongdong Wang, Yanli Zhao, Zhichao Jin, Yonggui Robin Chi
Summary: This research introduces a novel catalytic strategy to modulate the thermodynamics and control the enantioselectivities of asymmetric aldol reactions via post-aldol processes. By using an NHC catalyst to activate a masked enolate substrate, the study successfully achieves enantioselective acylative kinetic resolution, resulting in acylated aldol products with high optical purities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Toni Hashimoto, Kaoru Kato, Reiko Yano, Tomoki Natori, Hiroki Miura, Ryo Takeuchi
JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Inorganic & Nuclear
Yutaka Matsubara, Takamichi Yamaguchi, Toru Hashimoto, Yoshitaka Yamaguchi
Article
Chemistry, Inorganic & Nuclear
Shintaro Ono, Takashi Watanabe, Yosuke Nakamura, Hiroyasu Sato, Toru Hashimoto, Yoshitaka Yamaguchi
Article
Chemistry, Inorganic & Nuclear
Erika Asano, Yuki Hatayama, Nobutaka Kurisu, Atsufumi Ohtani, Toru Hashimoto, Youji Kurihara, Kazuyoshi Ueda, Shinji Ishihara, Hirotaka Nagao, Yoshitaka Yamaguchi
DALTON TRANSACTIONS
(2018)
Article
Chemistry, Inorganic & Nuclear
Daichi Takaki, Kenichi Ogata, Youji Kurihara, Kazuyoshi Ueda, Toru Hashimoto, Yoshitaka Yamaguchi
INORGANICA CHIMICA ACTA
(2018)
Article
Chemistry, Organic
Ryo Takeuchi, Shunsuke Fujisawa, Yuzo Yoshida, Jun Sagano, Tom Hashimoto, Asuka Matsunami
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Inorganic & Nuclear
Nobutaka Kurisu, Erika Asano, Yuki Hatayama, Youji Kurihara, Toru Hashimoto, Kei Funatsu, Kazuyoshi Ueda, Yoshitaka Yamaguchi
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2019)
Article
Chemistry, Applied
Toru Hashimoto, Tsubasa Maruyama, Takamichi Yamaguchi, Yutaka Matsubara, Yoshitaka Yamaguchi
ADVANCED SYNTHESIS & CATALYSIS
(2019)
Article
Biochemistry & Molecular Biology
Toru Hashimoto, Kei Funatsu, Atsufumi Ohtani, Erika Asano, Yoshitaka Yamaguchi
Article
Chemistry, Organic
Toru Hashimoto, Keisuke Shiota, Yoshitaka Yamaguchi
Article
Chemistry, Applied
Toru Hashimoto, Keisuke Shiota, Kei Funatsu, Yoshitaka Yamaguchi
Summary: A nickel-catalyzed cross-coupling reaction between aryl halides and primary or secondary aliphatic alcohols has been achieved using a bench-stable nickel complex supported by a monoanionic O,N,N-tridentate ligand. The reaction proceeds smoothly without the need for a phosphine ligand, giving moderate to good yields of alkyl aryl ethers.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Toru Hashimoto, Tsubasa Maruyama, Toshiya Ishimaru, Masaru Matsugaki, Keisuke Shiota, Yoshitaka Yamaguchi
Summary: A Wacker-Tsuji-Type oxidation reaction using molecular oxygen and TMDS catalyzed by ferrate has been developed for the oxidation of styrene derivatives to ketones, with good yields. The system can also achieve cleavage of the C-C double bond of alpha-phenyl-substituted styrene derivatives to provide one-carbon-degraded ketones in good yield.
Article
Chemistry, Organic
Toru Hashimoto, Keisuke Shiota, Toshiya Ishimaru, Yoshitaka Yamaguchi
Summary: A new method for the hydrosilylation reaction of alkenes has been developed using 1,1,3,3-tetramethyldisiloxane as a substitute for Me2SiH2, catalyzed by a nickel-pincer complex with a monoanionic O,N,P-tridentate ligand under mild reaction conditions. The reaction proceeds smoothly with high yields and high Markovnikov selectivity for styrene derivatives. The protocol shows a wide substrate scope and compatibility with various functional groups, including secondary hydrosilanes.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Toru Hashimoto, Kohei Nishikimura, Makoto Hojo
Summary: Triphenylsilane (Ph3SiH) acts as a Lewis-acidic catalyst for the ring-opening reaction of di- and tri-substituted epoxides with alcohols, leading to the synthesis of ss-alkoxy alcohols under nearly neutral reaction conditions. This straightforward protocol enables the facile synthesis of ss-alkoxy alcohols with high yields.
Article
Chemistry, Multidisciplinary
Toru Hashimoto, Toshiya Ishimaru, Keisuke Shiota, Yoshitaka Yamaguchi
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
