Bibliographies thématiques / Symmetric/Asymmetric Catalysis

Littérature scientifique sur le sujet « Symmetric/Asymmetric Catalysis »

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Publié le 7 septembre 2023

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Articles de revues sur le sujet "Symmetric/Asymmetric Catalysis"

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Wang, Xiao-Chen, Zhao-Ying Yang et Ming Zhang. « Synthesis and Applications of Chiral Bicyclic Bisborane Catalysts ». Synthesis 54, no 06 (19 novembre 2021) : 1527–36. http://dx.doi.org/10.1055/a-1701-7679.

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AbstractThe development of chiral borane Lewis acid catalysts opened the door for transition-metal-free catalyzed asymmetric organic reactions. Herein, we have summarized our work on the preparation of two classes of novel chiral bicyclic bisborane Lewis acid catalysts derived from C 2-symmetric [3.3.0] dienes and [4.4] dienes, respectively. These catalysts not only form frustrated Lewis pairs with Lewis bases to catalyze asymmetric hydrogenation reactions but also activate Lewis basic functional groups in traditional Lewis acid catalyzed asymmetric reactions.1 Introduction2 Synthesis of C 2-Symmetric Fused Bicyclic Bisborane Catalysts and Their Use in Imine Hydrogenation3 Synthesis of Spiro Bicyclic Bisborane Catalysts and Their Use in ­N-Heteroarene Reduction4 Other Types of Asymmetric Reactions Promoted by Chiral ­Bicyclic Bisborane Catalysts5 Conclusion
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Desimoni, Giovanni, Giuseppe Faita et Karl Anker Jørgensen. « C2-Symmetric Chiral Bis(Oxazoline) Ligands in Asymmetric Catalysis ». Chemical Reviews 106, no 9 (septembre 2006) : 3561–651. http://dx.doi.org/10.1021/cr0505324.

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Henderson, Alexander S., John F. Bower et M. Carmen Galan. « Carbohydrate-based N-heterocyclic carbenes for enantioselective catalysis ». Org. Biomol. Chem. 12, no 45 (2014) : 9180–83. http://dx.doi.org/10.1039/c4ob02056a.

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Versatile syntheses of C2-linked and C2-symmetric carbohydrate-based NHC·HCls from functionalised amino-carbohydrate derivatives are reported. The corresponding Rh complexes were evaluated in asymmetric hydrosilylation of ketones.
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Litwinienko, Grzegorz, Gino A. DiLabio et K. U. Ingold. « A theoretical and experimental investigation of some unusual intermolecular hydrogen-bond IR bands — Appearances can be deceptive ». Canadian Journal of Chemistry 84, no 10 (1 octobre 2006) : 1371–79. http://dx.doi.org/10.1139/v06-097.

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The IR spectra of the O-H stretch for hydrogen bonds (HBs) arising from complex formation between the HB donor (HBD), 4-fluorophenol, and the HB acceptors, peroxides and ethers, frequently show asymmetry that appears to arise from two incompletely resolved bands from two different complexes, but the O-H HB bands with the HBD methanol are symmetric (M. Berthelot, F. Bessau, and C. Laurence. Eur. J. Org. Chem. 925 (1998)). The present studies show that this difference in O-H HB band shapes also is true for other phenols and alcohols. However with ethylene oxide, 4-fluorophenol gives an almost symmetric O-H HB band with a very broad maximum, while alcohols give symmetric O-H HB bands with well-defined maxima. It is shown by experiment that the unusual O-H HB band shapes for the phenols are not due to Fermi resonance and are unrelated to the enthalpies of HB complex formation. Theoretical exploration of the potential energy (PE) surfaces for complexes of 4-fluorophenol and methanol with tert-butyl methyl ether and ethylene oxide reveals that O-H HB band asymmetry or broadness cannot be ascribed to the presence of two different HB complexes. For this ether, the PE surfaces for rotation about the HB and for up-and-down motion of the HBD with respect to the COC plane of the ether are relatively symmetric for methanol, but are strongly asymmetric for 4-fluorophenol, hence the differences in the O-H HB band shapes. The PE surfaces for the epoxide are effectively symmetric, but the PE for rotation about the HB has a single broad minimum for methanol, whereas with 4-fluorophenol there are two minima owing to attractive interactions between the phenyl group and the CH2 groups of the epoxide. The previously unknown β2H values for ethylene oxide and tetramethylethylene oxide are 0.36 and 0.58, respectively.Key words: asymmetric IR O-H bands, asymmetric potential energy surfaces, hydrogen-bonded complexes, hydrogen bond enthalpy, O-H frequency shift.
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Ruppel, Joshua V., Xin Cui, Xue Xu et X. Peter Zhang. « Stereoselective intramolecular cyclopropanation of α-diazoacetates via Co(ii)-based metalloradical catalysis ». Org. Chem. Front. 1, no 5 (2014) : 515–20. http://dx.doi.org/10.1039/c4qo00041b.

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Costabile, Chiara, Stefania Pragliola et Fabia Grisi. « C2-Symmetric N-Heterocyclic Carbenes in Asymmetric Transition-Metal Catalysis ». Symmetry 14, no 8 (5 août 2022) : 1615. http://dx.doi.org/10.3390/sym14081615.

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The last decades have witnessed a rapid growth of applications of N-heterocyclic carbenes (NHCs) in different chemistry fields. Due to their unique steric and electronic properties, NHCs have become a powerful tool in coordination chemistry, allowing the preparation of stable metal-ligand frameworks with both main group metals and transition metals. An overview on the use of five membered monodentate C2-symmetric N-heterocyclic carbenes (NHCs) as ligands for transition-metal complexes and their most relevant applications in asymmetric catalysis is offered.
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Castillón, Sergio, Carmen Claver et Yolanda Díaz. « C1 and C2-symmetric carbohydrate phosphorus ligands in asymmetric catalysis ». Chemical Society Reviews 34, no 8 (2005) : 702. http://dx.doi.org/10.1039/b400361f.

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Vogl, Erasmus M., Shigeki Matsunaga, Motomu Kanai, Takehiko Iida et Masakatsu Shibasaki. « Linking BINOL : C2-symmetric ligands for investigations on asymmetric catalysis ». Tetrahedron Letters 39, no 43 (octobre 1998) : 7917–20. http://dx.doi.org/10.1016/s0040-4039(98)01756-0.

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Al-Majid, Abdullah M., Brian L. Booth et Jonnes T. Gomes. « C2-Symmetric Ligands for Asymmetric Catalysis based on Feist's Acid ». Journal of Chemical Research, no 2 (1998) : 78–79. http://dx.doi.org/10.1039/a706185d.

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van Slagmaat, Christian A. M. R., Khi Chhay Chou, Lukas Morick, Darya Hadavi, Burgert Blom et Stefaan M. A. De Wildeman. « Synthesis and Catalytic Application of Knölker-Type Iron Complexes with a Novel Asymmetric Cyclopentadienone Ligand Design ». Catalysts 9, no 10 (22 septembre 2019) : 790. http://dx.doi.org/10.3390/catal9100790.

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Asymmetric catalysis is an essential tool in modern chemistry, but increasing environmental concerns demand the development of new catalysts based on cheap, abundant, and less toxic iron. As a result, Knölker-type catalysts have emerged as a promising class of iron catalysts for various chemical transformations, notably the hydrogenation of carbonyls and imines, while asymmetric versions are still under exploration to achieve optimal enantio-selectivities. In this work, we report a novel asymmetric design of a Knölker-type catalyst, in which the C2-rotational symmetric cyclopentadienone ligand possesses chiral substituents on the 2- and 5-positions near the active site. Four examples of the highly modular catalyst design were synthesized via standard organic procedures, and their structures were confirmed with NMR, IR, MS, and polarimetry analysis. Density functional theory (DFT) calculations were conducted to elucidate the spatial conformation of the catalysts, and therewith to rationalize the influence of structural alterations. Transfer- and H2-mediated hydrogenations were successfully established, leading to appreciable enantiomeric excesses (ee) values up to 70%. Amongst all reported Knölker-type catalysts, our catalyst design achieves one of the highest ee values for hydrogenation of acetophenone and related compounds.
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Thèses sur le sujet "Symmetric/Asymmetric Catalysis"

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Axe, Philip. « Pseudo-C3-symmetric titanium complexes for asymmetric catalysis ». Thesis, University of Bath, 2008. https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.512296.

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Luo, Yunfei. « Chemoenzymatic synthesis of C2 symmetric chiral dienes for asymmetric catalysis ». Thesis, University of Liverpool, 2010. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.539483.

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Böhnisch, Torben. « C2-Symmetric Pyrazole-Bridged Ligands and Their Application in Asymmetric Transition-Metal Catalysis ». Doctoral thesis, Niedersächsische Staats- und Universitätsbibliothek Göttingen, 2015. http://hdl.handle.net/11858/00-1735-0000-0028-876A-6.

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Lake, Fredrik. « C2- and C3-symmetric ligands via ring-opening of aziridines ». Doctoral thesis, KTH, Chemistry, 2002. http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-3424.

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This thesis deals with the design and synthesis of chiralenantiopure nitrogencontaining ligands and the use of theseligands in asymmetric catalysis. A modular synthetic approachto enantiopure nitrogen-containing ligands was developed. Thesynthetic method is based on the ring-opening of activatedchiral aziridines by nitrogen nucleophiles. The aziridines areconveniently prepared from amino alcohols. The structure oftheaziridine and of the nucleophile can be extensively varied andlibraries of ligands are easily prepared. The use of primaryamines affords C2-symmetric bis(sulfonamides), whereas the use ofammonia affords C3-symmetric tris(sulfonamides) that can beelaborated into the corresponding tetra-amines.

The C2- and C3-symmetric ligands were used in the asymmetrictitaniummediated addition of diethylzinc to benzaldehyderesulting in modest enantioselection, 76% ee. A thoroughinvestigation of the reaction conditions revealed that theamount of Ti(OiPr)4has a decisive effect on the reaction rate and thestereochemical outcome of the reaction. The reaction timedecreased from about 90 hours to 15 minutes and theenantioselectivity changed from 26% of the (R)- enantiomer to72% of the (S)-enantiomer when the Ti(OiPr)4:benzaldehyde ratio was increased from 0.125:1 to1.48:1. Moreover, the titanium-mediated addition of diethylzincto benzaldehyde was studied in the presence of chiraladditives. The bis(sulfonamides) were also used in thecyclopropanation of cinnamyl alcohol. However, only lowenantioselection was observed, 27% ee.

The C3-symmetric tetra-amines were reacted to formazaphosphatranes. These weak acids were only partiallydeprotonated by the strong base KOtBu to form the correspondingproazaphosphatranes. The unexpectedly strong basicity of theproazaphosphatranes was believed to be due to steric effects assuggested by DFT calculations. The tetra-amines and thesulfonamides were used for the preparation of metal complexesof Lewis acidic metals such as titanium(IV) andzirconium(IV).

Keywords:asymmetric catalysis, aziridine, benzaldehyde,diethylzinc, enantioselective, ligand, proazaphosphatrane,ring-opening, sulfonamide, symmetry, titanium, zirconium

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Böhnisch, Torben [Verfasser], Franc [Akademischer Betreuer] [Gutachter] Meyer, Guido [Gutachter] Clever, Thomas [Gutachter] Waitz, Ulf [Gutachter] Diederichsen, Dietmar [Gutachter] Stalke et Konrad [Gutachter] Koszinowski. « C2-Symmetric Pyrazole-Bridged Ligands and Their Application in Asymmetric Transition-Metal Catalysis / Torben Böhnisch. Betreuer : Franc Meyer. Gutachter : Franc Meyer ; Guido Clever ; Thomas Waitz ; Ulf Diederichsen ; Dietmar Stalke ; Konrad Koszinowski ». Göttingen : Niedersächsische Staats- und Universitätsbibliothek Göttingen, 2016. http://d-nb.info/1103233963/34.

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Gillespie, Jason A. « Design and synthesis of wide bite angle phosphacyclic ligands ». Thesis, University of St Andrews, 2012. http://hdl.handle.net/10023/3100.

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By examining structure activity relationships for a given catalytic reaction it is possible to discover what ligand features and parameters lead to stable and highly active/selective catalyst systems. With this knowledge in hand it may be possible to rationally design next generation ligands and catalysts to affect improved substrate transformations, with higher selectivities and faster reaction times. The success of Burk's DuPhos ligands in asymmetric hydrogenation demonstrated that chiral phosphacycles can be a potent source of chiral induction, whilst in a similar vein the work of van Leeuwen and Kamer established the wide bite angle xanthene based ligands as excellent catalysts in a range of reactions including hydroformylation. In a preliminary study with Osborne they showed that combining these wide bite angle ligand backbones with Burk's phospholane moieties led to a new powerful ligand in asymmetric allylic substitution. To examine the potential of combining these two ligand features further we designed and synthesised nine new C2-symmetric bidentate wide bite angle bisphosphacyclic ligands, featuring phosphetane, phospholane or diazaphospholane rings, aiming at a wide diversity of steric and electronic properties. The application of these ligands as chiral auxiliaries in transition metal catalysed reactions, including; hydrogenation, hydrocyanation, hydroformylation and allylic alkylation has been investigated. Good to excellent enantioselectivities were observed in all reactions, with maximum ee's of 92.5% observed in hydrogenation, using N-(3,4-dihydro-1-napthalenyl)-acetamide as substrate, and of 96.2% in the alkylation of 1,3-diphenyl-2-propenyl acetate.
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Fjellander, Ester. « Self-adaptable catalysts : Importance of flexibility and applications in asymmetric catalysis ». Doctoral thesis, KTH, Organisk kemi, 2010. http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-12852.

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The topic of this thesis is the design and synthesis of biaryl-based self adaptableligands for asymmetric metal catalysis. The results discussed in papers I-III are covered, together with some unpublished results concerning substrate-adaptable catalysts. A general survey of self-adaptable catalysts is presented first. The second chapter of this thesis starts with a survey of inversion barriers in biphenyl-based ligands and catalysts. Thereafter, the determination of barriers to conformational adaptation in dibenzoazepines and dibenzophosphepines is described. Palladium complexes with a diphosphine ligand or a diamine ligand, as well as the free diamine ligand, were studied. Entropies and enthalpies of activation were determined with variable temperature NMR spectroscopy. The mechanism of conformational change in the metal complexes was elucidated. The third chapter describes the synthesis of semiflexible and rigid phosphinite ligands, as well as their application in rhodium-catalysed asymmetric hydrogenation. Modest enantioselectivities (up to 63% ee) were obtained. The semiflexible ligand was found to behave like the most active rigid diastereomer. The fourth chapter describes the behaviour of amine and phosphoramidite ligands in model complexes relevant to the palladium-catalysed asymmetricallylic alkylation of benchmark substrates. Diphosphoramidite and aminephosphoramiditeligands were designed and synthesised. Pd(olefin) complexesof diamine and diphosphoramidite ligands were studied, and their symmetry determined. It was found that both types of ligands are able to adapt their conformation to the substrate.
QC20100630
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Hunt, Jamie. « C1- and C2- Symmetrical Metal-Salen Complexes and their Application to Asymmetric Catalysis ». Thesis, University of Newcastle Upon Tyne, 2010. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.515075.

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Stranne, Robert. « Investigation of Symmetry and Electronic Effects in Asymmetric Palladium-Catalysed Allylic Substitutions ». Doctoral thesis, KTH, Chemistry, 2001. http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-3283.

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Zalubovskis, Raivis. « Flexibility – a tool for chirality control in asymmetric catalysis ». Doctoral thesis, KTH, Kemi, 2006. http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-4166.

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This thesis deals with the design and synthesis of ligands for asymmetric catalysis: palladium catalyzed allylic alkylations, and rho-dium and iridium catalyzed hydrogenations of olefins. Chirally flexible phosphepine ligands based on biphenyl were synthesized and their properties were studied. The rotation barrier for configurationally flexible phosphepines was determined by NMR spectroscopy. The ratio of the atropisomers was shown to depend on the group bound to phosphorus. Only complexes with two homochiral ligands bound to the metal center were observed upon complexation with Rh(I). It was shown that one diastereomer of the flexible ligand exhibits higher activity but lower selectivity than its diastereomer in the rhodium catalyzed hydrogenation of methyl alfa-acetamidocinnamate. These ligands were also tested in nickel catalyzed silabora-tions. Chiral P,N-ligands with pseudo-C2 and pseudo-CS symmetry based on pyrrolidines-phospholanes or azepines-phosphepines were synthesized and studied in palladium catalyzed allylic alkylations. Semi-flexible azepine-phosphepine based ligands were prepared and their ability to adopt pseudo-C2 or pseudo-CS symmetry depending on the substrate in allylic alkylations was studied. It was shown on model allyl systems with flexible N,N-ligands that the ligand prefers CS-symmetry in compexes with anti-anti as well as syn-syn allyl moieties, but that for the latter type of complexes, according to computations, the configuration of the ligand is R*,R* in the olefin complexes formed after addition of a nucleophile to the allylic group. A preliminary investigation of the possibilities to use a su-pramolecular approach for the preparation of P,N-ligands with pseudo-C2 and pseudo-S symmetry was made. An N,N-ligand with C2 symmetry was prepared and its activity in palladium catalyzed ally-lic alkylation was studied. Pyridine-based P,N-ligands were tested in iridium catalyzed hy-drogenations of unfunctionalized olefins with good activities and se-lectivities. In order to attempt to improve the selectivity, ligands with a chirally flexible phosphepine fragment were prepared and applied in catalysis with promising results.
QC 20100929
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Livres sur le sujet "Symmetric/Asymmetric Catalysis"

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Harald, Gröger, dir. Asymmetric organocatalysis : From biomimetic concepts to applications in asymmetric synthesis. Weinheim : Wiley-VCH, 2005.

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Berkessel, Albrecht, Harald Gröger et David MacMillan. Asymmetric Organocatalysis : From Biomimetic Concepts to Applications in Asymmetric Synthesis. Wiley-VCH Verlag GmbH, 2005.

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Berkessel, Albrecht, Harald Gröger et David MacMillan. Asymmetric Organocatalysis : From Biomimetic Concepts to Applications in Asymmetric Synthesis. Wiley & Sons, Incorporated, John, 2006.

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Chapitres de livres sur le sujet "Symmetric/Asymmetric Catalysis"

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Gamez, P., F. Fache, M. Lemaire et P. Mangeney. « Heterogeneous Asymmetric Catalysis with C2 Symmetric Amine-Modified Rhodium/Silica ». Dans Chiral Reactions in Heterogeneous Catalysis, 147–49. Boston, MA : Springer US, 1995. http://dx.doi.org/10.1007/978-1-4615-1909-6_16.

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Zhang, Wanbin, et Delong Liu. « Symmetrical 1,1′-Bidentate Ferrocenyl Ligands ». Dans Chiral Ferrocenes in Asymmetric Catalysis, 175–214. Weinheim, Germany : Wiley-VCH Verlag GmbH & Co. KGaA, 2010. http://dx.doi.org/10.1002/9783527628841.ch7.

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Keyes, Michael C., et William B. Tolman. « Chiral C3-symmetric ligands and their transition metal complexes ». Dans Asymmetric Catalysis, 189–219. Elsevier, 1998. http://dx.doi.org/10.1016/s1874-5156(97)80009-1.

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Nakata, Kumi, Madoka Kawamura et Ryuichi Shirai. « Catalytic Asymmetric Epoxidation of Olefins by C2-Symmetric Chiral Dioxiranes ». Dans 19th International Congress on Heterocyclic Chemistry, 259. Elsevier, 2003. http://dx.doi.org/10.1016/b978-0-08-044304-1.50251-3.

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Bandar, Jeffrey S. « Reductions ». Dans Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0010.

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Manfred T. Reetz at the Max-Planck-Institut Mülheim and Philipps-Universität Marburg developed (J. Am. Chem. Soc. 2013, 135, 1665) a mutated Thermoethanolicus brockii alcohol dehydrogenase for the enantioselective reduc­tion of 4-alkylidene cyclohexanone 1. Using a new C₂-symmetic chiral bisphos­phine ligand (Wingphos, 5), Wenjun Tang at the Shanghai Institute of Organic Chemistry reported (Angew. Chem. Int. Ed. 2013, 52, 4235) the rhodium-catalyzed asymmetric hydrogenation of β-aryl enamide 3. Qi-Lin Zhou of Nankai University utilized chiral spirophosphine oxazoline iridium complexes 8a and 8b for the asymmetric hydrogenation of unsaturated piperidine carboxylic acid 6 (Angew. Chem. Int. Ed. 2013, 52, 6072) and 1,1-diarylethylene 9 (Angew. Chem. Int. Ed. 2013, 52, 1556) with excellent selectivities. The iron- catalyzed chemoselective hydrogenation of α,β-unsaturated aldehyde 11 was demonstrated (Angew. Chem. Int. Ed. 2013, 52, 5120) by Matthias Beller at the University of Rostock. Jeffrey S. Johnson at the University of North Carolina at Chapel Hill showed (J. Am. Chem. Soc. 2013, 135, 594) that asymmetric trans­fer hydrogenation of racemic acyl phosphonate 14 yielded β-stereogenic α- hydroxy phosphonate 16, a reversal in diastereoselectivity observed in the case of α-keto ester analogues. Gojko Lalic of the University of Washington developed (Org. Lett. 2013, 15, 1112) a monophasic copper catalyst system for the selective semireduction of terminal alkyne 17. Alois Fürstner and coworkers at Max-Planck-Institut Mülheim reported (Angew. Chem. Int. Ed. 2013, 52, 355) the ruthenium-catalyzed trans- selective hydro­genation of alkyne 19. Macrocyclic alkynes could also be selectively hydrogenated to E- alkenes using this methodology. Bernhard Breit at the University of Freiburg found (Angew. Chem. Int. Ed. 2013, 52, 2231) that a bimetallic Pd/ Re/ graphite catalyst system was highly active for the hydrogenation of tertiary amide 21 to amine 22. Professor Beller also discovered (Chem. Eur. J. 2013, 19, 4437) that a commercially available ruthenium complex allowed for the effective transfer hydrogenation of aromatic nitrile 23 to benzyl amine 24. Notably, no reductive amination side products were observed. Maurice Brookhart at the University of North Carolina at Chapel Hill used (Org. Lett. 2013, 15, 496) tris(pentafluorophenyl)borane as a highly active catalyst for the selective reduction of carboxylic acid 25 to aldehyde 26 with triethylsilane as a hydride source.
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