Article
Chemistry, Physical
Aleksandra Buchcic-Szychowska, Anna Zawisza, Stanislaw Lesniak, Michal Rachwalski
Summary: In this study, chiral aziridine-phosphines were used as catalysts in the asymmetric Morita-Baylis-Hillman reaction. The desired chiral products were obtained in moderate to high yields and with a high enantiomeric excess. The use of enantiomeric pairs of catalysts led to the formation of products with opposite absolute configurations.
Article
Chemistry, Multidisciplinary
Peng Chen, Shun-Zhong Tan, Lei Zhu, Qin Ouyang, Zhi-Jun Jia, Wei Du, Ying-Chun Chen
Summary: In this study, a Pd-0 catalyst mediated the regio- and enantioselective aza-Morita-Baylis-Hillman (MBH) reaction of α,β,γ,δ-unsaturated systems by using a δ-Lewis base as the catalyst. The reaction involved the dehydrogenative reaction of γ,δ-unsaturated compounds to produce electron-poor dienes, which then underwent regioselective umpolung Friedel-Crafts-type addition to imines through the auto-tandem Pd-0-π-Lewis base catalysis. After β-H elimination, chemically inverse aza-MBH-type adducts with excellent enantioselectivity were obtained.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Naruhiro Gondo, Koki Fujimura, Ryuichi Hyakutake, Yoshihiro Ueda, Takeo Kawabata
Summary: Asymmetric regioselective vinylogous aza-Morita-Baylis-Hillman reactions were conducted using organocatalysis. The reactions between 3-vinylcyclopentenone and various aldimines, in the presence of chiral pyrrolidinopyridine catalysts, yielded 7-adducts with high regioselectivity and moderate enantioselectivity.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Organic
Futao Peng, Liliang Huang, Junhai Huang, Huangdi Feng
Summary: The Aza-Morita-Baylis-Hillman cascade strategy mediated by 1,4-diazabicyclo-[2.2.2]octane (DABCO) was utilized to efficiently produce amino derived 1,6-dienes using a variety of primary amines. Surprisingly, using an aqueous medium promoted reaction efficiency and increased product yield. The protocol demonstrated significant advances in synthetic chemistry and pharmaceutical chemistry with its one-pot operation, high chemoselectivity, and broad substrate scope.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Naruhiro Gondo, Ryuichi Hyakutake, Koki Fujimura, Yoshihiro Ueda, Katsuhiko Nakano, Ryosuke Tsutsumi, Masahiro Yamanaka, Takeo Kawabata
Summary: In this study, catalyst-controlled vinylogous aza-MBH reactions of vinylcyclopentenone were conducted, showing that DABCO-catalysis led to exclusive formation of alpha-adducts while DMAP-catalysis predominantly produced gamma-adducts. It was found that the rate-determining step for the DABCO-catalyzed reactions was the Mannich-type C-C bond forming step, while for the DMAP-catalyzed reactions, it appeared to be the beta-elimination step.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Lei Zhang, Wangzhen Bao, Yuchen Liang, Wenjing Pan, Dongyang Li, Lichun Kong, Zhi-Xiang Wang, Bo Peng
Summary: This study demonstrates the reversal of stereoselectivity in MBH-type [3,3]-rearrangement by using a new pair of rearrangement partners, leading to the synthesis of different types of alpha-aryl alpha,beta-unsaturated carbonyl derivatives. Mechanistic studies provide insights into the reaction pathway and the opposite stereoselectivities observed.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Prashant Shukla, Ambika Asati, Devkumari Patel, Manorama Singh, Vijai K. K. Rai, Ankita Rai
Summary: This study reports on the Morita Baylis-Hillman (MBH) reaction using various aldehydes with acrylonitrile and methyl acrylate as electron-deficient alkenes. A novel catalyst, EDC.HCl, is utilized in the presence of CuI to synthesize the MBH adduct. The synthetic protocol shows excellent product yield (up to 99%), ambient reaction conditions, shorter reaction time, and no side product formation.
Article
Chemistry, Physical
Ricardo Lucas Gomes Pimentel, Rodolfo B. da Silva, Mario Luiz Araujo de Almeida Vasconcellos, Claudio Gabriel Lima-Junior, Fausthon F. da Silva
Summary: This study explores the synthesis and characterization of a mixed-metal copper-manganese iminodiacetate 1D coordination polymer (Cu/Mn-IDA) and its application as a catalyst for the Morita-Baylis-Hillman reaction. The results demonstrate that under optimized conditions, the catalyst can achieve yields of up to 87% for various aldehyde substrates. Additionally, the catalyst exhibits good recyclability.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Organic
Jianning Liao, Jipan Dong, Jiaqing Xu, Wei Wang, Yongjun Wu, Yuxia Hou, Hongchao Guo
Summary: A phosphine-catalyzed [3 + 2] annulation reaction has been developed in this study to synthesize multifunctional isoxazoles with moderate to good yields and diastereoselectivities. The use of a spirocyclic chiral phosphine catalyst resulted in up to 89% ee.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yue Wang, Manman Song, Er-Qing Li, Zheng Duan
Summary: This study presents a new palladium/phosphine cooperative catalytic system for the synthesis of bicyclo[3.1.0]hexene derivatives, highlighting the crucial roles of both Pd and phosphine in the selective intermolecular activation of Morita-Baylis-Hillman carbonates. This strategy opens up a new avenue for efficient and economical metal/Lewis base dual catalytic systems and provides valuable clues on solving the limitations of selective activation.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Sebastiano Mantovani, Angela Pintus, Alessandro Kovtun, Giulio Bertuzzi, Manuela Melucci, Marco Bandini
Summary: A metal-free synthetic approach to functionalized indenes using graphene oxide (GO) is presented in this article. The method involves intramolecular Friedel-Crafts-type allylic alkylations with Morita-Baylis-Hillman alcohols. Experimental and spectroscopic investigations were conducted to understand the reaction mechanism involving a nanostructured carbon material-based C-C bond forming reaction. The results showed that this carbocatalysis approach is a viable option for the synthesis of indenes, with a wide scope and moderate to high yield under mild reaction conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Physical
Hugo Santos, Lucas A. Zeoly, Manoel T. Rodrigues Jr, Fabio S. Fernandes, Ralph C. Gomes, Wanda P. Almeida, Fernando Coelho
Summary: Since its discovery in the late 1960s, the Morita-Baylis-Hillman (MBH) reaction has been a powerful carbon-carbon sigma-bond-forming reaction, producing small polyfunctionalized molecules. Advances in functional catalysts and reaction conditions have been made to improve the reaction rate, substrate scope, and enantioselectivity. This review provides an updated summary of the main improvements in catalytic systems for the MBH reaction over the past decade until nowadays, aiming to inspire further investigations and overcome the remaining challenges of this fascinating transformation.
Article
Chemistry, Organic
Siyu Wang, Lianyou Zheng, Shutao Wang, Shulin Ning, Zhuoqi Zhang, Jinbao Xiang
Summary: A base- and catalyst-free C(sp(3))-H allylic alkylation of 2-alkylpyridines with Morita-Baylis-Hillman (MBH) carbonates is described, involving a plausible mechanism of tandem S(N)2' type nucleophilic substitution followed by an azaCope rearrangement. Various alkyl substituents on 2-alkylpyridines were tolerated in the reaction to give the allylation products in 26-91% yields. The developed method provides a straightforward and operational simple strategy for the allylic functionalization of 2-alkypyridine derivatives.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Parasitology
Ana Carolina Santana Vieira, Mariana da Silva Santos, Anderson Brandao Leite, Amanda Evelyn da Silva, Luiz Henrique Agra Cavalcante-Silva, Gabrielle de Souza Augusto Pereira, Sany Delany Gomes Marques, Barbara Viviana de Oliveira Santos, Alysson Wagner Fernandes Duarte, Aline Cavalcante de Queiroz, Kristerson Reinaldo de Luna-Freire, Magna Suzana Alexandre-Moreira
Summary: Leishmaniasis is a neglected disease with limited treatment options and adverse effects. This study evaluated the antileishmanial activity of several derivatives and found that one derivative (1G) showed activity against both promastigote and amastigote forms with low toxicity to macrophages.
PARASITOLOGY RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Lucas Raposo Carvalho, Lucas Gil Venturelli, Thiago Castro Lopes, Eclair Venturini Venturini Filho, Vinicius Goncalves Fontenelle, Guilherme Ferreira de Lima, Leila Lea Yuan Visconte, Eder do Couto Tavares
Summary: Eliminating N-nitrosamines from rubber products is a challenge for the industry, and allyldithiocarbimate salts can be a viable alternative to traditional accelerators, offering better performance.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Medicinal
Ari Hardianto, Fei Liu, Shoba Ranganathan
JOURNAL OF CHEMICAL INFORMATION AND MODELING
(2018)
Article
Chemistry, Organic
Sviatoslav S. Eliseenko, Fei Liu
Article
Biochemistry & Molecular Biology
Michael P. Gotsbacher, Sung Min Cho, Nam Hee Kim, Fei Liu, Ho Jeong Kwon, Peter Karuso
ACS CHEMICAL BIOLOGY
(2019)
Article
Biochemical Research Methods
Ari Hardianto, Varun Khanna, Fei Liu, Shoba Ranganathan
BMC BIOINFORMATICS
(2019)
Article
Biotechnology & Applied Microbiology
Payal Barua, Seong Beom Ahn, Abidali Mohamedali, Fei Liu
BIOTECHNOLOGY LETTERS
(2020)
Article
Chemistry, Medicinal
Sviatoslav S. Eliseenko, Mohan Bhadbhade, Fei Liu
Article
Biochemistry & Molecular Biology
Jerran Santos, Sibasish Dolai, Matthew B. O'Rourke, Fei Liu, Matthew P. Padula, Mark P. Molloy, Bruce K. Milthorpe
Summary: The differentiation of human adipose derived stem cells towards a neural phenotype using small molecules has been a popular research topic, and proteomic profiling has revealed the changes in enriched proteins at different timepoints. These unique proteins identified play critical roles in neurogenic differentiation.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Article
Chemistry, Organic
Ryan T. Kenny, Fei Liu
Summary: A robust synthesis of Soai-type pyrimidine aldehydes was achieved by controlled formation and quenching of a lithiated pyrimidine intermediate. The optimized rate of n-BuLi addition synchronized with the addition to ethyl formate, resulting in consistently high yields of 2-alkylpyrimidinecarboxaldehydes, which can be used in autocatalysis or as functionalized synthons.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Jinling Liu, Yinghua Yu, Xueliang Huang
Summary: Deuterated compounds are important in pharmaceutical chemistry and the selective incorporation of deuterium atoms onto pharmacophore-containing compounds is of great interest. In this study, a concise method for constructing deuterated dibenzo-fused epsilon-lactones and epsilon-lactams through Pd-catalyzed carbene bridging C-D bond activation strategy was described. Deuterated ortho-bromobenzaldehydes were readily available reactants and deuterium atoms were selectively incorporated at the dibenylic position with high deuterated ratio.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Oncology
Rajdeep Chakraborty, Charbel Darido, Fei Liu, Maciej Maselko, Shoba Ranganathan
Summary: Immune therapies have shown promising results in the treatment of head and neck cancer by boosting the patient's immune system to fight tumor spread. This review highlights recent clinical success in the field of head and neck cancer immunotherapy, including the development of immune checkpoint inhibitors and a human papilloma virus vaccine. The review also emphasizes the importance of understanding basic biology and implementing personalized immunotherapy for better treatment outcomes.
Article
Multidisciplinary Sciences
Rajdeep Chakraborty, Charbel Darido, Arthur Chien, Aidan Tay, Karen Vickery, Honghua Hu, Fei Liu, Shoba Ranganathan
Summary: The role of Gipie in adenoid cystic carcinoma (ACC) and mucoepidermoid carcinoma (A-253) was evaluated in this study. Results showed that silencing Gipie led to morphological changes in the cells, increased apoptosis, decreased T regulatory cells, and increased activated NK cells.
SCIENTIFIC REPORTS
(2023)
Article
Chemistry, Medicinal
Ivan de Jesus Salazar-Estrada, Karthik Shantharam Kamath, Fei Liu
Summary: The SADL approach utilizes two covalent modifiers under a common ligand directive for precise protein labeling, improving target selectivity and labeling precision, broadening protein identification opportunities, aiding in understanding biological or disease mechanisms, and accelerating drug target discovery.
ACS PHARMACOLOGY & TRANSLATIONAL SCIENCE
(2022)
Review
Biochemistry & Molecular Biology
Miaomiao Liu, Peter Karuso, Yunjiang Feng, Esther Kellenberger, Fei Liu, Can Wang, Ronald J. Quinn
Article
Biochemical Research Methods
Ari Hardianto, Muhammad Yusuf, Fei Liu, Shoba Ranganathan
BMC BIOINFORMATICS
(2017)
Article
Chemistry, Multidisciplinary
Alexander F. Moore, David J. Newman, Shoba Ranganathan, Fei Liu
AUSTRALIAN JOURNAL OF CHEMISTRY
(2018)
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)
