• Cp*Ir complexes bearing a chiral N -(2-picolyl)sulfonamidato catalyze a convenient asymmetric reductive amination of benzylic ketones using readily available β-amino alcohols as chiral aminating agents. (organic-chemistry.org)
  • Chiral amines are broadly used compounds in pharmaceutical industry and organic synthesis, and reductive amination reactions have been the most appreciated methods for their syntheses. (sustech.edu.cn)
  • However, one-step transfer hydrogenative direct asymmetric reductive amination (THDARA) that could expand the scope, simplify the operation and eliminate the use of additives has been challenging. (sustech.edu.cn)
  • In this work, based on the Xiao's racemic transfer hydrogenative reductive amination in 2010 and our recent work in novel chiral pyridine ligands, chiral half-sandwich iridium catalysts were rationally designed and synthesized. (sustech.edu.cn)
  • succeeded in the direct asymmetric reductive amination for the synthesis of chiral β-arylamines . (chemistryviews.org)
  • These IREDs can reduce preformed imines as well as intermolecular reductive amination. (matthey.com)
  • All our IREDs catalyse reductive amination of ketones with small aliphatic amines. (matthey.com)
  • A selection of the IREDs are capable of accepting bulky aniline derivatives as the amine donor molecule in intermolecular reductive amination. (matthey.com)
  • Amines also plays a role in important reactions like Hofmann degradation, Gabriel synthesis, reductive amination, and Hofmann rearrangement. (neetexambooster.in)
  • Amines can undergo the reductive amination, a reaction where a carbonyl compound reacts with an amine and a reducing agent to form an amine. (neetexambooster.in)
  • The labeling process utilizes reductive amination. (biosyn.com)
  • Reductive amination is also part of the Maillard reaction. (biosyn.com)
  • Understanding and Overcoming the Limitations of Bacillus badius and Caldalkalibacillus thermarum Amine Dehydrogenases for Biocatalytic Reductive Amination. (novartis.com)
  • They draw inspiration from a common synthetic method known as reductive amination (Figure 1). (chembites.org)
  • Both reactive manifolds can meet at this point, and the aldehyde (1) can be converted to the alkylated amine product (7) directly via an enzyme-catalyzed reductive amination using a reductive aminase and the biological reductant NADPH as a source of electrons. (chembites.org)
  • Nonetheless, it is remarkable to witness the synergy between biological systems and organic chemical platforms like reductive amination. (chembites.org)
  • One such method uses reductive amination to tag the glycan with either of the two fluorescent heterobifunctional linkers, 2-amino-N-(2-aminoethyl)-benzamide (AEAB) or em p /em -nitrophenyl anthranilate (PNPA) 19,20. (ebat2018.org)
  • We compared the binding properties of glycans, which were coupled to AEAB either through reductive amination (open-ring, OR) or acryloylation (closed-ring, CR) 20, and examined glycan acknowledgement using glycan microarrays. (ebat2018.org)
  • For most glycan K 858 binding proteins (those focusing on an epitope in the non-reducing end) binding was unaffected from the conjugation method, but antibody acknowledgement of some epitopes was damaged by reductive amination. (ebat2018.org)
  • The 1-(3,4-methylenedioxyphenyl)-3-butanamines (HMDAs) are prepared via reductive amination of the corresponding ketone with a series of low molecular weight alkylamines. (erowid.org)
  • AuPd−Fe3O4 Nanoparticle Catalysts for Highly Selective, One‐Pot Cascade Nitro‐Reduction and Reductive Amination" Cho, A. (snu.ac.kr)
  • Palladium complexes containing chiral phosphinooxazolines have been shown to be efficient catalysts for the Heck reaction. (wikipedia.org)
  • This work introduced a type of effective chiral catalysts for simplified approach to medicinally important chiral amines, as well as a rare example of robust enantioselective transition-metal catalysis. (sustech.edu.cn)
  • This transformation was enabled by utilizing chiral Pd-aqua complexes as combined Brønsted acid-base catalysts. (uni-leipzig.de)
  • As powerful chiral catalysts, strongly acidic imidodiphosphorimidates (IDPis) have been identified, which furnish the products with good yields and excellent enantioselectivity. (uni-leipzig.de)
  • Based upon their exceptional reactivity as cooperative Brønsted acid-base catalysts, chiral diphosphane Pd-aqua complexes have successfully been utilized in a broad range of asymmetric transformations. (uni-leipzig.de)
  • We report herein an asymmetric cooperative process for the enantioselective 1,6-addition of β-ketoesters to in situ generated para-quinone methides with chiral Pd−aqua complexes as mixed Brønsted acid−base catalysts. (uni-leipzig.de)
  • Our research in organic chemistry is focused on the development of efficient synthetic methodologies related to the synthesis of physiologically important compounds and the advancement of chiral catalysts aimed at practical asymmetric synthesis. (snu.ac.kr)
  • Using the optimized catalyst and azeotropic mixture of formic acid and triethylamine as the hydrogen source, a broad range of α-chiral (hetero)aryl amines, including various polar functional groups and heterocycles, were prepared in generally high yield and enantioselectivity under mild and operationally simple conditions. (sustech.edu.cn)
  • Direct Access to Chiral Aliphatic Amines by Catalytic Enantioconvergent Redox-neutral Amination of Alcohols. (wujiegroupnus.com)
  • Amines can be used as a chiral auxiliary groups in asymmetric synthesis. (neetexambooster.in)
  • The HIMS-Biocat group presents the first account of engineering an Escherichia coli strain for the in vivo conversion of racemic alcohols into α-chiral amines through the heterologous co-overexpression of alcohol dehydrogenases and an amine dehydrogenase. (hims-biocat.eu)
  • α-Chiral amines are pivotal building blocks for chemical manufacturing. (hims-biocat.eu)
  • Adding alkyl groups to amines constitutes an essential step en route to many pharmaceuticals, agrochemicals, resins, and polymers, but current methods require large amounts of compounds, high temperatures, long reaction times, or the use of toxic or expensive reagents. (chembites.org)
  • More specifically, in the Ir-catalyzed asymmetric allylic amination reactions with the Carreira phosphoramidite ligand [in ( S ) configuration] as the only chirality source, the target allylic amination products are isolated as the ( R )-isomers when the reactions are quenched at 5~10 min, but as the ( S )-isomers when the reactions are quenched at 8~11 h. (springernature.com)
  • The appropriate permutation of the four individual reaction rates (those of two enantiomers of the allylic precursors and two enantiomers of the allylic amination products) guarantees the isolation of each enantiomer of the allylic amination products in a highly enantioenriched form at different reaction time. (springernature.com)
  • 2023 ) Development of Immobilized Carreira (Phosphoramidite, Olefin) Ligands and Application in Iridium-Catalyzed Asymmetric Allylic Amination. (academictree.org)
  • Originally discovered by Sodeoka 25 years ago, they readily form reactive chiral Pd enolates upon deprotonation of b-dicarbonyl compounds and simultaneously, a Brønsted acid liberated from the catalyst activates the electrophile. (uni-leipzig.de)
  • In recent years, however, new developments towards the enantioselective synthesis of various heterocycles and other useful compounds have evolved which take advantage of the unique properties of chiral Pd-aqua complexes. (uni-leipzig.de)
  • 1) A bis-cyclometalated chiral-at-metal rhodium complex (designated as RhS) in combination with the photoredox catalyst [Ru(bpy)3](PF6)2 enables visible-light-activated asymmetric α-amination and α-alkylation of 2-acyl imidazoles with aryl azides or α-diazo carboxylic esters as radical precursors, respectively (Chapter 3.1). (uni-marburg.de)
  • Reetz, M. T. Palladium-Catalysed Amination of Aryl- and Heteroaryl Halides Using tert-Butyl Tetraisopropylphosphorodiamidite as an Easily Accessible and Air-Stable Ligand. (mpg.de)
  • Straightforward Synthesis of Chiral Sulfonate Based Ionic Liquids from Amino Alcohols for Chiral Recognition. (tu-clausthal.de)
  • The Bioreactions group is using enzymes as biocatalysts to support the synthesis of chiral building blocks and drug candidates, facilitating Novartis research from early discovery through to development. (novartis.com)
  • Phosphinooxazolines (often abbreviated PHOX) are a class of chiral ligands used in asymmetric catalysis. (wikipedia.org)
  • Bondarev, O. Chiral diphosphites and diphosphoramidites as cheap and efficient ligands in Rh-catalyzed asymmetric olefin hydrogenation. (mpg.de)
  • Sell, T. Mixtures of chiral monodentate phosphites, phosphonites and phosphines as ligands in Rh-catalyzed hydrogenation of N-acyl enamines: extension of the combinatorial approach. (mpg.de)
  • Mehler, G. Mixtures of chiral and achiral monodentate ligands in asymmetric Rh-catalyzed olefin hydrogenation: reversal of enantioselectivity. (mpg.de)
  • Mehler, G. A new principle in combinatorial asymmetric transition-metal catalysis: Mixtures of chiral monodentate P ligands. (mpg.de)
  • While these reaction products may be oxidized to give chiral alcohols, or subjected to C-C bond-forming homologation reactions, a simple and effective amination of boronic esters in a stereospecific fashion really wasn't available. (thieme.de)
  • Stereoselective amination of alcohols is receiving increased interest due to its higher atom-efficiency and overall improved environmental footprint compared with other chemocatalytic and biocatalytic methods. (hims-biocat.eu)
  • In summary, the present E. coli -ADH-AmDH system represents an important advancement towards the development of 'green', efficient and selective biocatalytic processes for the amination of alcohols. (hims-biocat.eu)
  • They are able to effect a wide range of substitutions including allylic alkylations (Tsuji-Trost reaction), aminations and sulfonylations. (wikipedia.org)
  • Chiral N‐triflyl phosphoramide was found an efficient catalyst for the enantioselective Friedel‐Crafts alkylation reaction of 4,7‐dihydroindole with β,γ‐unsaturated α‐keto esters. (deepdyve.com)
  • Herein we report an asymmetric two-component alkenyl Catellani reaction for the construction of C-N axial chirality through a pal-ladium/chiral norbornene cooperative catalysis and an axial-to-axial chirality transfer process. (authorea.com)
  • Access to both enantiomers of a chiral target compound typically relies on reversing the absolute configuration of the chiral component in the reaction system that is used to make them. (springernature.com)
  • A time-dependent enantiodivergent synthesis is reported in which the same enantiomer of a chiral catalyst can give both enantiomers of the product, depending on the reaction time. (springernature.com)
  • In asymmetric synthesis, certain chiral component in the reaction system, in any form of chiral substrate, auxiliary, reagent, catalyst or ligand, is required for the chirality transfer or amplification process. (springernature.com)
  • Recently, the research group led by Prof. Shu-Li You at Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences disclosed an unusual phenomenon in asymmetric catalysis, where the reaction time is found as the controlling factor to determine the absolute configuration of the chiral products. (springernature.com)
  • Comprehensive mechanistic studies reveal that the reason behind this unique time-dependent enantiodivergent synthesis phenomenon is that the same chiral Ir-catalyst promotes sequential kinetic resolution of allylic precursors and amination products with amine nucleophiles and the solvent methanol as the reaction partner, respectively. (springernature.com)
  • James Morken highlights his award-winning paper on a protocol for stereospecific amination of alkylboronic esters. (thieme.de)
  • The award-winning article deals with the direct stereospecific amination of primary, secondary, and tertiary alkylboronic esters. (thieme.de)
  • A concise method was developed to prepare chiral α‐monofluorinated‐β‐amino esters through N‐sulfinyl urea catalyzed asymmetric hydrosilylation of α‐fluoro‐β‐enamino esters, which affords high yields, good to high diastereoselectivities (up to>99/1), and moderate to good enantioselectivities (up. (deepdyve.com)
  • Abstract A carbene-catalyzed asymmetric access to chiral β-cyano carboxylic esters is disclosed. (stanford.edu)
  • Using chiral propargylic esters, bicyclic products were prepared in high optical purity by the intramolecular [5 + 2] cycloadditions. (degruyter.com)
  • Driving asymmetric catalysis with visible light or electricity is of significant value because they represent 'green' and sustainable methods to synthesize non-racemic chiral molecules and in addition offer ample opportunities for chemists to discover new mechanistic scenarios and invent previously. (uni-marburg.de)
  • This thesis presents novel applications of previously in the Meggers group developed chiral-at-metal rhodium complexes to the areas of asymmetric photocatalysis and asymmetric electrosynthesis. (uni-marburg.de)
  • Fürstner, A. Chiral heterobimetallic complexes of carbodiphosphoranes and phosphinidene-carbene adducts. (mpg.de)
  • Sell, T. Enantioselective hydrogenation of enamides catalyzed by chiral rhodium-monodentate phosphite complexes. (mpg.de)
  • All reactive intermediates remain bound to the chiral catalyst thereby providing a robust catalytic scheme (no exclusion of air necessary) with excellent stereoinduction. (uni-marburg.de)
  • Coordination of the cyclopropane with the chiral catalyst generates the visible-light-absorbing complex, lowers the reduction potential of the cyclopropane, and provides the asymmetric induction and overall stereocontrol. (uni-marburg.de)
  • The amino alcohol-derived chiral auxiliary was easily removed by mild periodic oxidants, leading to optically active primary β-arylamines without erosion of the optical purity. (organic-chemistry.org)
  • It is well known that a pair of enantiomers of given chiral molecules will probably exert different influences in living organism. (springernature.com)
  • In this regard, the preparation of both enantiomers of chiral molecules is highly demanding and thus a prominent task in asymmetric synthesis. (springernature.com)
  • It is the common strategy to switch the absolute configuration of the chiral component if the opposite enantiomer of the target chiral molecules is expected. (springernature.com)
  • Chris engineered our evergreen HeWT to make it enantioselective in the synthesis of the smallest chiral amine, 2 amino butane. (paradisiresearch.com)
  • 2018 ) Development of C-Symmetric Chiral Bifunctional Triamines: Synthesis and Application in Asymmetric Organocatalysis. (academictree.org)
  • 2018 ) Desymmetrisation of meso-diones promoted by a highly recyclable polymer-supported chiral phosphoric acid catalyst Rsc Advances . (academictree.org)
  • 2) A bis-cyclometalated chiral-at-metal rhodium complex (designated as RhO) is demonstrated to catalyze stereocontrolled chemistry of photo-generated radicals and at the same time an enantioselective sulfonyl radical addition to alkenes (Chapter 3.2). (uni-marburg.de)
  • We are currently working on expanding the scope of this reactivity pattern, and checking whether it will contribute to the fast generation of useful chiral molecule libraries for medicinal chemistry. (springernature.com)
  • Density functional theory (DFT) calculation of the catalytically active Ir−H species and the key hydride transfer step supported the chiral pyridine-induced stereospecific generation of the iridium center, and the enantioselection by taming the highly flexible key transition structure with multiple attractive non-covalent interactions. (sustech.edu.cn)
  • was generated by linking -mannan disaccharides to a protein via click chemistry, and it was found that stereo-diversification of the linker region with a mixture of anomers in the chiral carbons enhanced immunity to the proximal disaccharide portion 16,17. (ebat2018.org)
  • People have learned a lesson from the thalidomide tragedy on the importance of evaluating both enantiomers of any chiral drug candidate before it comes into the market. (springernature.com)
  • They are able to effect a wide range of substitutions including allylic alkylations (Tsuji-Trost reaction), aminations and sulfonylations. (wikipedia.org)
  • Yi-Yong Huang of the Wuhan University of Technology used a chiral phosphoric acid to mediate the enantioselective addition of the allylic boronate 36 to the aldehyde 35 . (organic-chemistry.org)
  • Tsarev V. N., Konkin S. I., Loim N. M., Kelbysheva E. S., Popova L. N., Petrovskii P. V., Davankov V. A., Gavrilov K. N.: Novel planar chiral phosphite: Preparation and use in the synthesis of Pd(II) complexes and in Pd-catalyzed allylic alkylation. (iupac.org)
  • While these reaction products may be oxidized to give chiral alcohols, or subjected to C-C bond-forming homologation reactions, a simple and effective amination of boronic esters in a stereospecific fashion really wasn't available. (thieme.de)
  • Development of Novel Chiral Hypervalent Iodine(V) Reagents and Their Applications for Enantioselective Reactions (Fac. (csj.jp)
  • Di-adamantylalkylphosphine, known as cataCXium ® A, is a bulky and electron-rich phosphine ligand used for Heck and Suzuki couplings, Buchwald-Hartwig amination of arylchlorides, and α-arylation reactions of ketones. (sigmaaldrich.com)
  • 20. Highly enantio- and diastereoselective organocatalytic cascade aza-Michael-Michael reactions: a direct method for the synthesis of trisubstituted chiral pyrrolidines. (nih.gov)
  • Then how to use aldehydes or ketones plus ammonia and reduction to give a chiral amine. (yale.edu)
  • A selection of the IREDs are capable of accepting bulky aniline derivatives as the amine donor molecule in intermolecular reductive amination. (matthey.com)
  • The protocol was suitable for substrates containing a wide range of functional groups and provided remote chiral amine products with high levels of regio- and enantioselectivity. (mit.edu)
  • A chiral HPLC method was promptly developed and the protected amine was subjected to a screening study. (galchimia.com)
  • A rapid construction of enantioenriched benzo-fused quinolizidines, indolizidines, and their analogues by ruthenium-catalyzed asymmetric cascade hydrogenation/reductive amination of quinolinyl- and quinoxalinyl-containing ketones has been developed. (unboundmedicine.com)
  • We found that photolysis of Mn2(CO)10 enables radical addition to chiral N-acylhydrazones using a broad range of precursors, including primary alkyl halides and multifunctional compounds. (uiowa.edu)
  • Catalytic asymmetric Tsuji-Trost benzylation is a promising strategy for the preparation of chiral benzylic compounds. (bvsalud.org)
  • Computational Study of Enantioselectivity in the Asymmetric Allylation of Aldehydes with Chiral Pt(II) Phosphinite Complexes. (acs.org)
  • 17. One-pot synthesis of alpha-carbolines via sequential palladium-catalyzed aryl amination and intramolecular arylation. (nih.gov)
  • Our chiral N-acylhydrazones have proved to be broadly useful acceptors for additions of alkyl radicals and a wide range of nucleophiles including hydride and allylsilane reagents. (uiowa.edu)
  • We have also described a new synthetic route to 1,2-disubstituted 1,2,3,4-tetrahydropyrrole[1,2-a]pyrazines, which involves the diastereoselective addition of Grignard reagents to chiral oxazolidines. (unibo.it)
  • Taking in account the results obtained in alternative 1, only one solvent was chosen and the pool of chiral reagents was expanded to eight. (galchimia.com)
  • TY - JOUR T1 - Rapid Construction of Structurally Diverse Quinolizidines, Indolizidines, and Their Analogues via Ruthenium-Catalyzed Asymmetric Cascade Hydrogenation/Reductive Amination. (unboundmedicine.com)
  • Moreover, sometimes the old-fashioned racemic resolution of a chiral compound is not only a good option, but an essential step in the development of a New Chemical Entity. (galchimia.com)
  • Breit B , Hilpert L, Sieger S, Haydl A . Palladium- and Rhodium-Catalyzed Dynamic Kinetic Resolution of Racemic Internal Allenes Towards Chiral Pyrazoles. (academictree.org)
  • N-Ligand-Enabled Aromatic Nucleophilic Amination of 1,2-Diaryl- o -Carboranes with (R 2 N) 2 Mg for Selective Synthesis of 4-R 2 N- o -Carboranes and 2-R 2 N- m -Carboranes. (edu.hk)
  • Asymmetric Dual Chiral Catalysis using Iridium Phosphoramidites and Diarylprolinol Silyl Ethers: Insights into Stereodivergence. (iitb.ac.in)
  • Breit B , Haydl A , Hilpert L. Regioconvergent and Enantioselective Rhodium-Catalyzed Hydroamination of Internal and Terminal Alkynes: A Highly Flexible Access to Chiral Pyrazoles. (academictree.org)
  • On the other hand, alternatives 2 and 3 would allow the introduction of an expensive building block in a latter stage, thus reducing costs, but synthetic steps should be tested and chiral HPLC methods should be developed. (galchimia.com)
  • Alternative 1 would be faster because the route was already established and a chiral HPLC method for ee determination had been developed by our client. (galchimia.com)
  • En route to life: The very first step. (univ-grenoble-alpes.fr)
  • However, development of the chiral HPLC method was also troublesome and, when the samples of a screening study were assayed, the results were disappointing. (galchimia.com)
  • Forero-Cortés PA, Haydl AM . The 25th Anniversary of the Buchwald-Hartwig Amination: Development, Applications, and Outlook Organic Process Research & Development . (academictree.org)
  • The target products can be converted into other structurally complex chiral indoles without the loss of enantioselectivities. (bvsalud.org)
  • A number of chiral myths exist related to pharmaceutical products. (galchimia.com)
  • The compound presents a chiral center in that position and initial assays showed that the S -enantiomer presented better activity than the R -isomer. (galchimia.com)