Article
Chemistry, Multidisciplinary
Jade Dussart-Gautheret, Julie Yu, Krithika Ganesh, Gaikwad Rajendra, Fabrice Gallou, Bruce H. Lipshutz
Summary: This study describes the surfactant-enabled asymmetric ATA-catalyzed reductive aminations in water, which enhance the conversion levels and enable 1-pot chemoenzymatic catalysis. The modified conditions involving both biocatalysis and chemocatalysis are environmentally responsible, indicating the potential of using chemistry in water.
Article
Chemistry, Multidisciplinary
J. Daniel Bailey, Edward Helbling, Amey Mankar, Matthew Stirling, Fred Hicks, David K. Leahy
Summary: Reducing or eliminating organic solvent use in pharmaceutical manufacturing is a highly effective way to reduce environmental, health, and safety impacts. The process described utilizing primarily water-based methods significantly reduces material inputs and organic solvent use, while surprisingly using less water and improving overall yield compared to traditional methods.
Article
Chemistry, Multidisciplinary
Matthias Elfinger, Timon Schoenauer, Sabrina L. J. Thomae, Robert Staeglich, Markus Drechsler, Mirijam Zobel, Juergen Senker, Rhett Kempe
Summary: The 3D metal catalyst developed here utilizes hydrogen as the reducing agent and easily handled ammonia dissolved in water as the nitrogen source for the synthesis of primary amines. The catalyst operates under mild conditions and outperforms commercially available noble metal catalysts. The key to its high activity is the unique support material it uses.
Article
Chemistry, Multidisciplinary
Weixi Kong, Yunting Liu, Chen Huang, Liya Zhou, Jing Gao, Nicholas J. Turner, Yanjun Jiang
Summary: We report the engineering of an amine dehydrogenase (AmDH) from Jeotgalicoccus aerolatus for the direct asymmetric reductive amination of heteroaryl ketones. The engineered enzyme exhibited excellent conversions and enantioselectivities, even for ketones with bulky alkyl chains. Directed evolution based on molecular docking was used to enhance the enzyme's activity by enlarging the active pocket with a more hydrophobic entrance. The engineered enzyme was also applied in the synthesis of pharmaceutically relevant amines and a key intermediate of chiral pincer ligands.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Hao Song, Yao Xiao, Zhuohua Zhang, Wanjin Xiong, Ren Wang, Liangcheng Guo, Taigang Zhou
Summary: A new synthetic method for the selective transfer hydrogenation of nitriles to primary amine-boranes and secondary amines has been developed. The method demonstrates high selectivity and yields up to 95%, and has been successfully applied in the synthesis of N-15 labeled compounds with an 89% yield.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Giuseppe Faudone, Iris Bischoff-Kont, Lea Rachor, Sabine Willems, Rezart Zhubi, Astrid Kaiser, Apirat Chaikuad, Stefan Knapp, Robert Fuerst, Jan Heering, Daniel Merk
Summary: TLX, a ligand-sensing transcription factor, plays a crucial role in neuronal stem cell homeostasis and shows therapeutic potential in neurodegenerative diseases and central nervous system tumors. Through profiling a drug fragment collection, researchers identified propranolol as the strongest TLX agonist, which can counteract glioblastoma cell proliferation and migration. This study provides a collection of TLX modulators as potential chemical tools for therapeutic intervention in glioblastoma.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Fengwei Chang, Chengyi Wang, Qipeng Chen, Yongjin Zhang, Guohua Liu
Summary: The combination of biocatalysis and transition-metal catalysis can bridge synthetic gaps in chemical or biological processes, but the deactivation between enzymatic and chemical species poses a significant challenge. Researchers developed an encapsulated Au/carbene and free amine dehydrogenase co-catalyst system, enabling efficient hydration/amination enantioselective cascade reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Zhaofeng Gao, Jingwen Liu, Haizhou Huang, Huiling Geng, Mingxin Chang
Summary: The research reports on efforts to merge two asymmetric reductive amination reactions into a single-step transformation, utilizing specific catalyst and acid additives to successfully synthesize enantiopure secondary amine products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Qijie Zou, Wei Zhang, Haoyue Wang, Guangwei Yin, Yongzhi He, Fangyi Li
Summary: The CF3 group attached to N-aryl hydrazone can be activated using a suitable base, making it an excellent C1 unit for assembling a series of 1,3,4-oxadiazoles through reaction with hydrazides. The reaction proceeds via the formation of a gem-difluorinated azoalkene intermediate. Furthermore, this reaction offers simple conditions and a broad substrate scope for both trifluoromethyl N-aryl hydrazones and hydrazides.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Matthieu Jouffroy, Thi-Mo Nguyen, Marie Cordier, Marielle Blot, Thierry Roisnel, Rafael Gramage-Doria
Summary: Direct reductive amination (DRA) is a widely used reaction in organic chemistry, aiming to convert carbonyl groups and amines into aminated compounds. The conventional method involves the use of a super stoichiometric amount of hazardous hydride reagents, which is incompatible with many sensitive functional groups. This study presents a new DRA method using iridium catalysis, overcoming the limitation of ketones with 2 degrees amines.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Soumyadeep Chakrabortty, Shasha Zheng, Fabian Kallmeier, Eszter Barath, Sergey Tin, Johannes G. de Vries
Summary: A readily available chiral Ru/bisphosphine catalyst was used to achieve the direct asymmetric reductive amination of bio-based levulinic acid (LA) to produce enantioenriched 5-methylpyrrolidinone with excellent enantioselectivity (up to 96% ee) and high isolated yield (up to 89%). Methyl levulinate (ML), a byproduct from the industrial production of 2,5-furandicarboxylic acid (FDCA), can be used as a substitute for LA with similar reactivity and selectivity. Mass spectrometry and isotope labelling studies suggest that the chiral lactam is formed through imine-enamine tautomerization/cyclization followed by asymmetric hydrogenation of the cyclic enamide.
Article
Chemistry, Organic
Xu-Kuan Qi, Lin Guo, Li-Juan Yao, Han Gao, Chao Yang, Wujiong Xia
Summary: A multicomponent carbonyl alkylative amination reaction using tetrabutylammonium decatungstate as a photocatalyst was described. Various N-arylamines, aldehydes, and hydrocarbons were examined as reaction substrates, yielding the corresponding alpha-branched tertiary and secondary amines in good to moderate yields. The reaction proceeds through the generation of alkyl radicals via a light-promoted hydrogen atom transfer process followed by free radical addition to iminium ions generated in situ.
Review
Chemistry, Organic
Jisna Jose, Elizabeth J. Diana, U. S. Kanchana, Thomas V. Mathew
Summary: Reductive amination is a valuable method for amine synthesis, which has been extensively studied in both academia and industry for a century. Amines and their derivatives are versatile building blocks for various organic substrates and play a significant role in the production of advanced chemicals, pharmaceuticals, polymers, and more. The development of innovative catalytic processes for the selective and sustainable synthesis of amines from readily available and environmentally friendly reagents remains a major focus in chemical research. Ruthenium catalysts have shown excellent performance in reductive amination due to their stability, selectivity, versatility, low toxicity, and high efficiency. This review provides a comprehensive overview of Ru-catalyzed reductive amination processes, covering the literature from 2009 to 2022.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Conor L. Oates, Alister S. Goodfellow, Michael Buehl, Matthew L. Clarke
Summary: A manganese catalyst with a P,N,N ligand that coordinates to the face of the metal catalyzes the hydrogenation of imines derived from indanone derivatives with high enantioselectivity. The generation of imines does not require an activating group and can be done in situ. The selectivity can be explained by DFT calculations.
Article
Chemistry, Multidisciplinary
Jun Zhang, Xin Li, Rongchang Chen, Xianwei Tan, Xiongduo Liu, Yaqing Ma, Fangfang Zhu, Chunyan An, Guangzheng Wei, Yongpeng Yao, Lujia Yang, Peng Zhang, Qiaqing Wu, Zhoutong Sun, Bin-Gui Wang, Shu-Shan Gao, Chengsen Cui
Summary: Imine reductases capable of accepting bulky amines have been identified using an increasing-molecule-volume-screening method, and an efficient gram-scale synthesis of an API sensipar analogue has been achieved.
COMMUNICATIONS CHEMISTRY
(2022)
Article
Chemistry, Organic
Ibrahim U. Kutama, Simon Jones
JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Organic
R. A. Bawa, F. -M. Gautier, H. Adams, A. J. H. M. Meijer, S. Jones
ORGANIC & BIOMOLECULAR CHEMISTRY
(2015)
Article
Cell Biology
Anne L. Robertson, Nikolay V. Ogryzko, Katherine M. Henry, Catherine A. Loynes, Matthew J. Foulkes, Marco M. Meloni, Xingang Wang, Christopher Ford, Malcolm Jackson, Philip W. Ingham, Heather L. Wilson, Stuart N. Farrow, Roberto Solari, Roderick J. Flower, Simon Jones, Moira K. B. Whyte, Stephen A. Renshaw
DISEASE MODELS & MECHANISMS
(2016)
Article
Chemistry, Organic
Rebecca C. Collins, Martyn N. Paley, Gillian M. Tozer, Simon Jones
TETRAHEDRON LETTERS
(2016)
Article
Chemistry, Inorganic & Nuclear
Christopher J. A. Warner, Andrew T. Reeder, Simon Jones
TETRAHEDRON-ASYMMETRY
(2016)
Article
Radiology, Nuclear Medicine & Medical Imaging
Steven Reynolds, Stephen Metcalf, Edward J. Cochrane, Rebecca C. Collins, Simon Jones, Martyn N. J. Paley, Gillian M. Tozer
MAGNETIC RESONANCE IN MEDICINE
(2017)
Article
Chemistry, Organic
X. Li, A. T. Reeder, F. Torri, H. Adams, S. Jones
ORGANIC & BIOMOLECULAR CHEMISTRY
(2017)
Article
Biology
Victoria A. Lund, Katarzyna Wacnik, Robert D. Turner, Bryony E. Cotterell, Christa G. Walther, Samuel J. Fenn, Fabian Grein, Adam J. M. Wollman, Mark C. Leake, Nicolas Olivier, Ashley Cadby, Stephane Mesnage, Simon Jones, Simon J. Foster
Article
Multidisciplinary Sciences
Matthew J. Foulkes, Katherine M. Henry, Julien Rougeot, Edward Hooper-Greenhill, Catherine A. Loynes, Phil Jeffrey, Angeleen Fleming, Caroline O. Savage, Annemarie H. Meijer, Simon Jones, Stephen A. Renshaw
SCIENTIFIC REPORTS
(2017)
Article
Chemistry, Organic
Alexander M. Fields, Simon Jones
Article
Chemistry, Organic
Christopher J. A. Warner, Sian S. Berry, Simon Jones
Article
Multidisciplinary Sciences
Matthew J. Foulkes, Faith H. Tolliday, Katherine M. Henry, Stephen A. Renshaw, Simon Jones
Article
Multidisciplinary Sciences
Peter Oatley, Joseph A. Kirk, Shuwen Ma, Simon Jones, Robert P. Fagan
SCIENTIFIC REPORTS
(2020)
Review
Chemistry, Organic
Sian S. Berry, Simon Jones
Summary: Chiral substituted pyrrolidines are key elements in biologically active molecules and are often synthesized using kinetic resolution methods to obtain enantiomerically pure compounds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Daniel Ray Jenkinson, Ashley James Cadby, Simon Jones
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
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)
