Article
Chemistry, Multidisciplinary
Ashley P. Mattey, Grayson J. Ford, Joan Citoler, Christopher Baldwin, James R. Marshall, Ryan B. Palmer, Matthew Thompson, Nicholas J. Turner, Sebastian C. Cosgrove, Sabine L. Flitsch
Summary: This study aimed to mimic the ability of eukaryotic cells to carry out multistep cascades, overcoming batch incompatibility by using continuous flow systems, and successfully achieving biocatalytic cascades with different aminating steps and introducing different amine reagents, ultimately synthesizing the target product.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Lu Ouyang, Rui Miao, Zhanhui Yang, Renshi Luo
Summary: Our Ir-catalyzed reductive amination of carboxylic acids with amines allows for the production of structurally diverse N-alkylated amines in good to excellent yields (up to 60 examples). This method offers mild conditions, convenient operations, and excellent functional group tolerance. The synthesis of Cinacalcet and (R)-Fendiline highlights the synthetic value of this protocol.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Peiyuan Yao, James R. Marshall, Zefei Xu, Jesmine Lim, Simon J. Charnock, Dunming Zhu, Nicholas J. Turner
Summary: In this study, a new stereoselective biocatalytic synthesis method for N-substituted alpha-amino esters was reported, utilizing diverse metagenomic imine reductases. Both enantiomers of the target products were synthesized with high conversion and excellent enantioselectivity under mild reaction conditions. Furthermore, over 20 different preparative scale transformations were performed, demonstrating the scalability of this system.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Xiao Xiao, Baoguo Zhao
Summary: Chemists are working to develop efficient methods for producing optically active compounds. Biomimetic asymmetric catalysis, which imitates enzymes, is an attractive strategy for producing chiral compounds. Recent research has focused on using chiral pyridoxals/pyridoxamines as catalysts to mimic enzymatic transamination and biological aldol reaction of glycine, and enable asymmetric biomimetic transamination and carbonyl catalysis of primary amines.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Chemistry, Multidisciplinary
Guangshou Feng, Colton K. Ku, Jiaqi Zhao, Qiu Wang
Summary: This paper reports an unprecedented three-component aminofluorination of alkenes and 1,3-dienes, which can achieve the synthesis of fi-fluoroalkylamines using innovative copper-catalyzed electrophilic amination strategy and alkylamine precursors. The method features high regioselectivity and good tolerance of various functional groups, providing a direct entry to a broad range of fi-fluorinated alkylamines.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Review
Chemistry, Inorganic & Nuclear
C. T. Nandhu, Thaipparambil Aneeja, Gopinathan Anilkumar
Summary: This review summarizes the recent advances in rhodium-catalyzed reductive amination, where rhodium complexes are employed as catalysts with high efficiency and good selectivity.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(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, Physical
Itziar Penafiel, Robert A. W. Dryfe, Nicholas J. Turner, Michael F. Greaney
Summary: The integration of electro and bio-catalysis offers new ways of making molecules under very mild, environmentally benign conditions. The combined process offers a new approach to amine alkylation with native alcohols, a key bond formation in the chemical economy that is currently achieved via precious metal-catalyzed hydrogen-borrowing technologies.
Article
Chemistry, Organic
Ziwei Huang, Zirui Lin, Jiexiong Mai, Shaohuan Lv, Feng Xie, Youxue Yuan, Wenbing Zhang, Fan Qian, Bin Li
Summary: This study describes a convenient and practical method for the synthesis of 2-cyano and 2-ester anilines via efficient and selective copper-catalyzed reductive amination. These compounds were successfully synthesized with good functional group tolerance. Furthermore, the synthesized compounds exhibited excellent fluorescent properties, which may have potential applications in the development of near-ultraviolet optical devices.
SYNTHESIS-STUTTGART
(2022)
Review
Chemistry, Multidisciplinary
Frank Hollmann, Diederik J. Opperman, Caroline E. Paul
Summary: This review highlights the synthetic state-of-the-art and potential of enzymes catalyzing reductions, ranging from carbonyl, enone, and aromatic reductions to reductive aminations. Enzymes play a key role in producing chiral products with new functionalities, leading to alternative synthetic routes for high-added-value compounds and bulk chemicals.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
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
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, Physical
Ziyuan Wang, Haisheng Zhou, Haoran Yu, Zhongji Pu, Jinling Xu, Hongyu Zhang, Jianping Wu, Lirong Yang
Summary: This study investigates the substrate recognition mechanism of glutamate dehydrogenase (GluDH) and develops a computational engineering strategy to redesign the binding pocket, leading to the synthesis of noncanonical amino acids. Tailor-made variants were created to improve the specific activities for producing high-value products. The computational enzyme redesign strategy shows promise in enhancing the production of noncanonical amino acids.
Article
Chemistry, Applied
Matthias Elfinger, Christof Bauer, Joerg Schmauch, Michael Moritz, Christoph Wichmann, Christian Papp, Rhett Kempe
Summary: This study presents an efficient method for the selective synthesis of differently substituted primary, secondary, and tertiary alkyl amines by combining borrowing hydrogen or hydrogen autotransfer and reductive amination with hydrogen. A nanostructured, bimetallic Co/Sc catalyst is used to mediate both reactions efficiently. The method shows broad product scope, good functional group tolerance, easy upscaling, and catalyst reusability.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Jeremy Steflik, Amelia Gilio, Michael Burns, Gideon Grogan, Rajesh Kumar, Russell Lewis, Carlos Martinez
Summary: This study reports a method for biocatalytic reductive amination reactions, which have high potential value in pharmaceutical synthesis. The researchers identified and engineered a RedAm enzyme to catalyze the synthesis of a key intermediate for a cyclin-dependent kinase (CDK) inhibitor. The optimized enzyme variant showed high productivity at high substrate concentrations (50-fold improvement over the wild-type). Crystal structures of both the wild-type and mutant enzymes were solved to elucidate the structural changes that improved the performance of the RedAm under process conditions. This work demonstrates the versatility and industrial utility of RedAm-catalyzed reductive amination by enabling the synthesis of a chiral intermediate on a multikilogram scale.
