Article
Chemistry, Multidisciplinary
David Egea-Arrebola, F. Wieland Goetzke, Stephen P. Fletcher
Summary: Rhodium-catalyzed enantioselective additions of aryl and vinyl boronic acids to cyclobutenone ketals are described in this work. The reaction involves enantioselective carbometalation to give cyclobutyl-rhodium intermediates, followed by beta-oxygen elimination to afford enantioenriched enol ethers. Overall, this addition serves as a surrogate for Rh-catalyzed 1,4-additions to cyclobutenone.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Naoki Yasukawa, Shuichi Nakamura
Summary: Catalytic enantioselective synthesis methodologies have been actively explored and developed to access valuable compounds such as unnatural alpha-amino acids. Asymmetric addition to ketimine-type electrophiles has been recognized as a powerful strategy, although it was limited a few decades ago. This feature article comprehensively overviews the research field and highlights the significant progress made, focusing on the chiral catalyst system and transition state as key parameters for such reactions.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Physical
Li-Ming Zhang, Wenjun Luo, Jiangzhen Fu, Yu Liu, Junliang Zhang
Summary: A newly developed PNP-type W-Phos ligand showed a unique effect on the catalytic asymmetric addition of reactive Grignard reagents to ketimines. This enabled a Cu(I)-catalyzed asymmetric alkylation reaction of N-sulfonyl ketimines, resulting in the formation of optically active α-tertiary amines with high enantioselectivities.
Article
Chemistry, Applied
An-Qi Miao, Meng Zhou, Jing-Long Chen, Shi-Chao Wang, Wen-Juan Hao, Shu-Jiang Tu, Bo Jiang
Summary: An asymmetric addition of arylboronic acids to pyrazolinone ketimines was reported using a palladium/chiral N,N'-disulfonyl bisimidazoline (Bim) catalytic system, yielding enantioenriched 4-amino-5-pyrazolones with high yields and high enantiomeric excess. The reaction demonstrated excellent compatibility between pyrazolinone ketimines and arylboronic acids, providing an enantioselective access to chiral aza-heterocycles bearing alpha-tertiary amines.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Jie Chen, Dong-yu Zhu, Xue-jing Zhang, Ming Yan
Summary: An enantioselective Michael addition has been developed for the synthesis of structurally diverse isatin-derived alpha-(trifluoromethyl)imine derivatives with excellent yields and enantioselectivities, which are valuable candidates for drug discovery.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Kaixuan Song, Min Wen, Kai Shen, Chaogang Fan, Zhenyu Yang, Shaohui Lin, Qinmin Pan
Summary: In this study, an asymmetric version of Pd(II)/bipyridine-catalyzed nucleophilic addition of arylboronic acids to N-sulfonyl arylaldimines was developed, achieving excellent asymmetric induction with the use of chiral pyridinooxazoline ligand (S)-t-BuPyOx. Moisture and oxygen-insensitive catalysis was realized under mild conditions, with 9 out of 16 examples giving 92-99% ee.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Jianrong Steve Zhou, Luoqiang Zhang, Xiuhua Wang, Maoping Pu, Caiyou Chen, Peng Yang, Yun-Dong Wu, Yonggui Robin Chi
Summary: Nickel catalysts with chiral pyrox ligands were used for enantioselective reductive arylation and heteroarylation of aldimines using (hetero)aryl halides and sulfonates. Crude aldimines generated from the condensation of aldehydes and azaaryl amines can also be used for catalytic arylation. The mechanism involves an elementary step of 1,4-addition of aryl nickel(I) complexes to N-azaaryl aldimines, as supported by density functional theory (DFT) calculations and experiments.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
An-Qi Cheng, Zeng-Hua Wu, Huai-Lan Yang, Wei-Liang Duan
Summary: A Pd-catalyzed asymmetric phosphination of alpha,beta-unsaturated sulfonyl fluorides was developed, resulting in a series of tertiary phosphorus compounds in high yields and enantioselectivities up to 99% ee. The chiral adduct can be further converted into chiral phosphine sulfonic acid as the ligand for the arene Ru metal complex.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Chihiro Homma, Taichi Kano, Keiji Maruoka
Summary: A bifunctional amino sulfonamide-catalyzed asymmetric conjugate addition of aldehydes to alkenyl alkynyl ketimines has been developed, yielding the desired conjugate adducts with high chemo-, diastereo- and enantioselectivity.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Mei Duan, Jingchao Chen, Ting Wang, Shaojian Luo, Meifen Wang, Baomin Fan
Summary: A wide range of chiral 3-amino-2-oxindoles were successfully synthesized with high optical purities through the enantioselective Friedel-Crafts addition of naphthols with isatin-derived ketimines using H8-BINOL-derived chiral biaryl phosphoric acid as the catalyst.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Christian J. Bettencourt, Tanja Krainz, Sharon Chow, Brendan T. Parr, William F. Tracy, Paul V. Bernhardt, Huw M. L. Davies, Craig M. Williams
Summary: The rhodium(II)-catalyzed reaction of a model alkenyl donor/ acceptor N-sulfonyltriazole with a wide selection of furans has been reported. A range of structurally diverse carbocyclic and ring-opened products were obtained, in good to excellent yields, via selective cyclopropanation or zwitterionic rearrangement pathways, depending on the structural and electronic features of the furan substrate.
Article
Chemistry, Organic
Ling-Zhi Sun, Xuan Yang, Nan-Nan Li, Meng Li, Qin Ouyang, Jian-Bo Xie
Summary: A facile synthetic method for 4-aryl-4,5-dihydropyrrole-3-carboxylates has been developed using a rhodium-catalyzed ring expansion strategy. This method offers a novel mechanism and enables asymmetric catalytic synthesis with excellent diastereoselectivity, leading to the formation of substituted pyrrolidines.
Article
Chemistry, Organic
David A. Gutierrez, James Fettinger, K. N. Houk, Kaori Ando, Jared T. Shaw
Summary: This study describes the Lewis-acid-promoted addition of prochiral E- and Z-allyl nucleophiles to chiral alpha-alkoxy N-tosyl imines with stereochemical control, resulting in the synthesis of two isomers of clausenamide.
Article
Chemistry, Organic
Jessica Wahlers, Michael Maloney, Farbod Salahi, Anthony R. Rosales, Paul Helquist, Per-Ola Norrby, Olaf Wiest
Summary: This study developed and applied a TSFF method to predict the stereoselectivity of aryl boronic acids conjugate addition to enones, achieving good results through automated screening and validation. Detailed error analysis and identification of structural origins for outliers were conducted. The results showed that the majority of virtual screening outcomes were in line with expectations.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Yu Yan, Wen-Cong Li, He Meng, Shufeng Chen, Jialin Ming, Tamio Hayashi
Summary: Racemic gamma-substituted alpha,beta-unsaturated gamma-lactams rac-1 reacted with arylboron reagents 2 in the presence of a chiral diene L1a-rhodium catalyst under basic conditions (3.0 equiv of NEt3) to give beta,gamma-disubstituted trans-gamma-lactams 3 with high diastereo- and enantioselectivity. This highly efficient dynamic kinetic resolution was achieved by fast racemization of 1 followed by kinetic resolution with the chiral rhodium catalyst. The synthetic utility of the method was demonstrated by the synthesis of key intermediates to biologically active compounds.
Article
Chemistry, Multidisciplinary
Miyuki Hatano, Takahiro Nishimura
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Article
Chemistry, Multidisciplinary
Midori Nagamoto, Takahiro Nishimura
CHEMICAL COMMUNICATIONS
(2015)
Article
Chemistry, Multidisciplinary
Midori Nagamoto, Takahiro Nishimura
CHEMICAL COMMUNICATIONS
(2015)
Article
Chemistry, Multidisciplinary
Ryosuke Takechi, Takahiro Nishimura
CHEMICAL COMMUNICATIONS
(2015)
Article
Chemistry, Multidisciplinary
Yusuke Ebe, Takahiro Nishimura
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2015)
Article
Chemistry, Organic
Takahiro Sawano, Minoru Hashizume, Shouta Nishimoto, Keiyu Ou, Takahiro Nishimura
Article
Chemistry, Multidisciplinary
Midori Nagamoto, Daisuke Yamauchi, Takahiro Nishimura
CHEMICAL COMMUNICATIONS
(2016)
Article
Chemistry, Multidisciplinary
Miyuki Hatano, Yusuke Ebe, Takahiro Nishimura, Hideki Yorimitsu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2016)
Article
Chemistry, Organic
Miyuki Hatano, Takahiro Nishimura, Hideki Yorimitsu
Article
Chemistry, Organic
Midori Nagamoto, Tomoyuki Yanagi, Takahiro Nishimura, Hideki Yorimitsu
Article
Chemistry, Organic
Takahiro Nishimura, Tomotaka Nagai, Ryosuke Takechi, Yusuke Ebe
SYNTHESIS-STUTTGART
(2016)
Article
Chemistry, Multidisciplinary
Midori Nagamoto, Takahiro Nishimura
CHEMICAL COMMUNICATIONS
(2014)
Article
Chemistry, Organic
Takahiro Sawano, Keiyu Ou, Takahiro Nishimura, Tamio Hayashi
JOURNAL OF ORGANIC CHEMISTRY
(2013)
Article
Chemistry, Multidisciplinary
Yusuke Ebe, Takahiro Nishimura
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2014)
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)