Article
Chemistry, Organic
Ling Qi, Pei-Jun Yang, Wen-Tao Ji, Gui-De Tao, Gaosheng Yang, Zhuo Chai
Summary: In this study, we report an efficient strategy for synthesizing compounds with high pharmaceutical value using catalysts. The method is simple and feasible, with mild reaction conditions, and can be used for the synthesis of important drugs.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Multidisciplinary Sciences
Aleksandra Buchcic-Szychowska, Stanislaw Lesniak, Michal Rachwalski
Summary: A series of chiral aziridines with a phosphine moiety were synthesized and used as organocatalysts in the asymmetric intramolecular Rauhut-Currier reactions of p-quinone derivatives. The desired chiral phenols were obtained with high yields and satisfactory enantiomeric excess values.
Article
Chemistry, Organic
Victor Garcia-Vazquez, Pablo Martinez-Pardo, Alexandru Postole, A. Ken Inge, Belen Martin-Matute
Summary: This study developed a method for synthesizing chiral trifluoromethylated aliphatic amines, which involves organocatalytic isomerization and imine/enamine reduction to obtain compounds with two noncontiguous stereogenic centers in high yields and selectivities. The method is effective for primary amine substrates and provides a new pathway for synthesizing chiral trifluoromethylated scaffolds.
Article
Chemistry, Multidisciplinary
Yuki Hirata, Daichi Sekine, Yoshimi Kato, Luqing Lin, Masahiro Kojima, Tatsuhiko Yoshino, Shigeki Matsunaga
Summary: In this study, the combination of an achiral cobalt(III) catalyst and a pseudo-C-2-symmetric H-8-binaphthyl chiral carboxylic acid was utilized for the asymmetric synthesis of benzothiadiazine-1-oxides containing a chiral sulfur center. The optimized protocol achieved high enantioselectivity and allowed for the synthesis of benzothiadiazine-1-oxides with various functional groups.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Kosuke Ohsawa, Junya Kubota, Shota Ochiai, Takayuki Doi
Summary: The stereoselective and short-step synthesis of N-protected allo-carnosadine, ent-carnosadine, and carnosadine lactam was achieved from a common cyclopropane intermediate. The key cyclopropane was obtained in excellent yield and optical purity through an inter-intramolecular double alkylation reaction. Subsequent monohydrolysis of the diester moiety under different reaction conditions provided diastereomers of monoacids, which were further converted to three carnosadine derivatives in 5-6 steps from the common diester.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Eiji Tayama, Nobuhiro Nakanome
Summary: The base-promoted alpha-alkylation of N-((S)-1-arylethyl)azetidine-2-carbonitriles via formation of their N-borane complexes was investigated. The method enables the production of optically active 2-substituted azetidine-2-carbonitriles with high yields.
Article
Chemistry, Multidisciplinary
Lan Zhou, Hong-Gang Cheng, Lisha Li, Kevin Wu, Jing Hou, Chengkang Jiao, Shuang Deng, Zirui Liu, Jin-Quan Yu, Qianghui Zhou
Summary: In this study, a modular platform for constructing planar chirality in 1,3-disubstituted ferrocenes/ruthenocenes via an enantioselective relay remote C-H activation strategy was developed. Various 1,3-disubstituted planar chiral metallocenes were prepared with high enantioselectivity (-96-. 99% e.e.). The resulting metallocenes can be easily derivatized for use as ligands and catalysts in asymmetric catalysis and as building blocks for other applications.
Article
Multidisciplinary Sciences
Marie L. J. Wong, Alistair J. Sterling, James J. Mousseau, Fernanda Duarte, Edward A. Anderson
Summary: Bicyclo[1.1.1]pentanes (BCPs) are essential in contemporary drug design, yet methods to access BCPs with adjacent stereocenters are limited. This study presents a photo- and organocatalyzed asymmetric addition of simple aldehydes to [1.1.1]propellane to generate enantioenriched alpha-chiral BCPs.
NATURE COMMUNICATIONS
(2021)
Article
Multidisciplinary Sciences
Jia-Lei Yan, Rakesh Maiti, Shi-Chao Ren, Weiyi Tian, Tingting Li, Jun Xu, Bivas Mondal, Zhichao Jin, Yonggui Robin Chi
Summary: In this study, a chiral solution utilizing N-heterocyclic carbene (NHC) catalyst was developed for the preparation of axially chiral styrenes with high enantioselectivity and excellent yields. The sulfone and carboxylic ester moieties in the styrenes are common functional groups in bioactive molecules and asymmetric catalysis.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Yan-Bo Li, Hu Tian, Shuai Zhang, Jun-Zhao Xiao, Liang Yin
Summary: In this study, a copper(I)-catalyzed reaction of diarylphosphines and O-benzoyl hydroxylamines was developed, leading to the synthesis of aminophosphinites and P-chiral aminophosphinites. The reaction mechanism was proposed and further transformation to P-chiral phosphines was achieved.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Yuya Nakagawa, Keigo Yamaguchi, Seijiro Hosokawa
Summary: The [3 + 2]-cycloaddition reaction between N-tosylaziridines and alpha,beta-unsaturated ketones was promoted with lithium iodide, providing high yields of the target products.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Donglei Wang, Ying-Bo Shao, Yunrong Chen, Xiao-Song Xue, Xiaoyu Yang
Summary: An efficient method for the asymmetric synthesis of planar-chiral macrocycles (paracyclophanes) has been developed using chiral phosphoric acid catalysis for enantioselective electrophilic aromatic aminations with azodicarboxylates. This method allows for the synthesis of a wide range of chiral macrocycles with varying ring sizes and functional groups, achieving high yields and enantioselectivities. The mechanism and origins of the stereoselectivities of these reactions were investigated through experimental studies and computational calculations. Preliminary utilization of the planar-chiral macrocycle as a chiral organocatalyst demonstrated the potential applications of these novel chiral skeletons.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Long-Tao Huang, Yuta Kitakawa, Kodai Yamada, Futa Kamiyama, Masahiro Kojima, Tatsuhiko Yoshino, Shigeki Matsunaga
Summary: We report the enantioselective synthesis of 1,2-benzothiazine 1-imines through C-H alkylation/cyclization reactions. This method utilizes sulfondiimines and sulfoxonium ylides to obtain cyclic sulfondiimine derivatives. The combination of [Ru(p-cymene)Cl-2](2) and a newly developed chiral spiro carboxylic acid is crucial for achieving high enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jin-Huang Peng, Yu-Qing Zheng, Li-Gang Bai, Wen-Bo Liu
Summary: Construction of axially chiral 1-azafluorenes via nickel-catalyzed [2+2+2] cycloaddition of alkynes and (o-alkynyl)benzyl nitriles is described. This strategy enables enantioselective discrimination of two sterically similar ortho substituents, such as H and F, during the construction of tri-ortho-substituted biaryl atropisomers. Mechanistic studies including the stereochemistry model and the stability of the atropenantiomers toward racemization are provided. The unique steric hindrance provided by 1-azafluorene skeleton and the fine chiral cavity of the nickel catalyst are key to achieving high enantioselectivity.
SCIENCE CHINA-CHEMISTRY
(2023)
Review
Chemistry, Organic
Helene Pellissier
Summary: This review provides an update on the field of asymmetric cascade palladium catalysis for the synthesis of chiral heterocycles since 2019. It demonstrates the use of diverse chiral palladium catalysts to promote unprecedented asymmetric domino reactions, leading to the direct synthesis of complex and densely functionalized chiral heterocyclic molecules.
CURRENT ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)