0000000000513172
AUTHOR
Reko Leino
showing 27 related works from this author
Chemoselective heterogeneous iridium catalyzed hydrogenation of cinnamalaniline
2020
International audience; Selective hydrogenation of unsaturated imines over heterogeneous catalysts is an ecologically feasible and effective way to produce commercially valuable saturated imines and unsaturated amines under mild conditions, avoiding the utilization of toxic halides. The liquid-phase hydrogenation of a model imine, cinnamalaniline, over Ir, Ru, Pd and Au catalysts was studied in polar protic (methanol, 2-propanol), polar aprotic (methyl tert-butyl ether) and non-polar aprotic (toluene) solvents at 40-80°C under atmospheric hydrogen pressure. Different metal oxides (Al 2 O 3 , ZrO 2 , SiO 2) and carbon composites based on carbon nitrides synthesized by pyrolysis of ethylenedi…
Synthesis of Chiral Catalyst Modifiers by Hydrosilylation of Cinchonidine and Their Application in the Hydrogenation of 1-Phenylpropane-1,2-dione and…
2005
Four new chiral modifiers were synthesized in order to investigate the effect of distal modifier substitution in the hydrogenation of ethyl pyruvate and 1-phenylpropane-1,2-dione on a supported Pt/Al2O3 catalyst. The chiral modifiers were prepared in good to moderate overall yields by Pt-catalyzed hydrosilylation of 9-O-TMS-protected cinchonidine with triethylsilane, triphenylsilane, bis(dimethylsilyl)ethane and (+)-(R)-methyl(1-naphthyl)phenylsilane followed by cleavage of the silyl ether protective group. Comparison of the synthesized modifiers in enantioselective hydrogenation using cinchonidine as reference modifier is reported, as well as details on their synthesis and characterization…
Thermal, spectroscopic and crystallographic analysis of mannose-derived linear polyols
2018
The major diastereomer formed in the Barbier-type metal-mediated allylation of D-mannose has previously been shown to adopt a perfectly linear conformation, both in solid state and in solution, resulting in the formation of hydrogen-bonded networks and subsequent aggregation from aqueous solution upon stirring. Here, a comprehensive study of the solid state structure of both the allylated D-mannose and its racemic form has been conducted. The binary melting point diagram of the system was determined by differential scanning calorimetry analysis, and the obtained results, along with structure determination by single crystal X-ray diffraction, confirmed that allylated mannose forms a true rac…
Racemization of Secondary-Amine-Containing Natural Products Using Heterogeneous Metal Catalysts
2018
Phase-selective low molecular weight organogelators derived from allylated D-mannose
2022
In the last decades, synthesis and design of low molecular weight organogelators has gained increasing attention due to their versatile use in, for example, cosmetics, biomedicine and oil spill remediation. In this work, three potential gelators have been prepared from allylated d-mannose. Both the gelators and the corresponding gels formed were thoroughly characterized by crystallography, FTIR spectroscopy, SEM, rheometry and NMR spectroscopy, in solution and in solid state. The results showed that two of the compounds phase-selectively form gels with hydrocarbon solvents. The most promising gelator compound is alkene terminated, with the unsaturated end functionality not critical for gel …
Cytotoxicities of Polysubstituted Chlorodicarbonyl(cyclopentadienyl) and (Indenyl)ruthenium Complexes
2013
Polysubstituted cyclopentadienyl and indenyl complexes of ruthenium were synthesized and investigated to elucidate their potential cytotoxic activities. In particular, substituted (indenyl)ruthenium complexes inhibited the proliferation of a panel of human adherent cancer cells with comparable activity to reference agent cisplatin. One of the active compounds exerted a concentration dependent inhibition of cell cycle at G1–S transiton as evidenced by flow cytometry.
Improved synthesis of Bn5CpRu(CO)2Cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of…
2010
An improved gram-scale synthesis of Bn5CpRu(CO)2Cl is reported based on heating of pentabenzylcyclopentadiene with Ru3(CO)12 at 160 °C under argon atmosphere in mesitylene followed by addition of chloroform, continued heating, and evaporation of the solvents. Subsequent washing of unreacted ligand precursor with hexane provided pure title compound in 77 % yield. In combination with Candida antarctica lipase B (CAL-B) (Novozym 435), this complex forms a highly active racemization catalyst for metallo-enzymatic dynamic kinetic resolution (DKR) of secondary alcohols as demonstrated in the present work by converting 100 g of racemic 1-phenylethanol to (R)-1-phenylethanol in >99 % ee and 93 %…
Cyclopenta[l]phenanthrenyl and Cyclopenta[a]acenaphthylenyl Half-Sandwich Complexes of Ruthenium as Racemization Catalysts for Secondary Alcohols
2008
Several half-sandwich complexes of ruthenium with cyclopenta[l]phenanthrenyl and cyclopenta[a]acenaphthylenyl ligands containing fused aromatic ring substituents on the cyclopentadienyl ring were p...
From Mannose to Small Amphiphilic Polyol: Perfect Linearity Leads To Spontaneous Aggregation
2016
Terminally unsaturated and diastereochemically pure polyol derived from d-mannose shows spontaneous aggregation behavior in water solution. In order to study and clarify this unforeseen phenomenon, a conformational study based on NMR spectroscopy combined with ab initio structure analysis using the COSMO-solvation model was pursued. The results, together with X-ray diffraction studies, suggest a low energy linear conformation for this particular substrate both in solid states and in solution. For such small-sized acyclic carbohydrate derivatives, the linear conformation appears to be a key prerequisite for the unusual molecular self-assembly reported herein. peerReviewed
A chiral diamine bis-phenolate complex of dioxomolybdenum(VI)
2009
Abstract A new dioxomolybdenum(VI) complex with a chiral tetradentate ligand is reported. The tripodal ligand containing two nitrogen atoms and two phenolic oxygen atoms was synthesized starting from a chiral diamine precursor. Further reaction with [MoO2(acac)2] yielded a monomeric molybdenum complex as a bright yellow solid. The structures of the molybdenum complex and the free diamine bis-phenol ligand were determined by X-ray diffraction.
Conformation of the galactose ring adopted in solution and in crystalline form as determined by experimental and DFT 1H NMR and single-crystal X-ray …
2003
The solution-state conformations of various galactose derivatives were determined by comparison of the experimental (1)H-(1)H vicinal coupling constants to those calculated using density functional theory (DFT) at the B3LYP/cc-pVTZ//B3LYP/6-31G(d,p) level of theory. The agreement between the experimental and calculated vicinal coupling constants for 1,2:3,4-di-O-isopropylidene-alpha-d-galactopyranose was good, thereby confirming an (O)S(2) skew conformation for it and its derivatives on the basis of their similar observed couplings. Single-crystal X-ray analysis of 1,2:3,4-di-O-isopropylidene-6-O-(3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-beta-d-glucopyranosyl)-alpha-d-galactopyranose and …
Improved synthesis and application of conjugation-amenable polyols from d-mannose
2019
A series of polyhydroxyl sulfides and triazoles was prepared by reacting allyl and propargyl d-mannose derivatives with selected thiols and azides in thiol-ene and Huisgen click reactions. Conformational analysis by NMR spectroscopy proved that the intrinsic rigidity and linear conformation of the mannose derived polyol backbone is retained in the final click products in solution. Single crystal X-ray structure determination of one of the compounds prepared further verified that the linear conformation of the polyol segment is also retained in the solid state. In addition, an improved method for direct Barbier-type propargylation of unprotected d-mannose is reported. The new reaction protoc…
Dicarbonylchloro(pentabenzylcyclopentadienyl)ruthenium as Racemization Catalyst in the Dynamic Kinetic Resolution of Secondary Alcohols
2009
Dicarbonylchloro(pentabenzylcyclopentadienyl)ruthenium has been prepared and its structure confirmed by X-ray analysis. This complex shows excellent catalytic activity and modest stability against air in racemization reactions of secondary alcohols. In Candida antarctica lipase B (CAL-B) catalyzed dynamic kinetic resolution (DKR) of 1-phenyl- and 1-(furan-2-yl)ethanol compounds, the new complex shows improved performance as an alcohol racemization catalyst in comparison with its well-known pentaphenylcyclopentadienyl analogue, hitherto considered as the leading catalyst candidate. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
A combined NMR, DFT, and X-ray investigation of some cinchona alkaloid O-ethers.
2008
Structures and conformational behavior of several cinchona alkaloid O-ethers in the solid state (X-ray), in solution (NMR and DFT), and in the gas phase (DFT) were investigated. In the crystal, O-phenylcinchonidine adopts the Open(3) conformation similar to cinchonidine, whereas the O-methyl ether derivatives of both cinchonidine and cinchonine are packed in the Closed(1) conformation. Dynamic equilibria in solutions of the alkaloids were revealed by combined experimental-theoretical spin simulation/iteration techniques for the first time. In the (1)H NMR spectra in CDCl3 and toluene-d8 at room temperature, Closed(1) conformation was observed for the O-silyl ethers as a separate set of sign…
Improved synthesis and application of conjugation-amenable polyols from d-mannose
2020
A series of polyhydroxyl sulfides and triazoles was prepared by reacting allyl and propargyl D-mannose derivatives with selected thiols and azides in thiol–ene and Huisgen click reactions. Conformational analysis by NMR spectroscopy proved that the intrinsic rigidity and linear conformation of the mannose derived polyol backbone is retained in the final click products in solution. Single crystal X-ray structure determination of one of the compounds prepared further verified that the linear conformation of the polyol segment is also retained in the solid state. In addition, an improved method for direct Barbier-type propargylation of unprotected D-mannose is reported. The new reaction protoc…
CCDC 713845: Experimental Crystal Structure Determination
2016
Related Article: Denys Mavrynsky, Mari Päiviö, Katri Lundell, Reijo Sillanpää, Liisa T. Kanerva, Reko Leino|2009|Eur.J.Org.Chem.|2009|1317|doi:10.1002/ejoc.200801248
CCDC 2149492: Experimental Crystal Structure Determination
2022
Related Article: Ida Mattsson, Manu Lahtinen, Ruzal Sitdikov, Bianca Wank, Tiina Saloranta-Simell, Reko Leino|2022|Carbohydr.Res.|518|108596|doi:10.1016/j.carres.2022.108596
CCDC 2149491: Experimental Crystal Structure Determination
2022
Related Article: Ida Mattsson, Manu Lahtinen, Ruzal Sitdikov, Bianca Wank, Tiina Saloranta-Simell, Reko Leino|2022|Carbohydr.Res.|518|108596|doi:10.1016/j.carres.2022.108596
CCDC 713844: Experimental Crystal Structure Determination
2016
Related Article: Denys Mavrynsky, Mari Päiviö, Katri Lundell, Reijo Sillanpää, Liisa T. Kanerva, Reko Leino|2009|Eur.J.Org.Chem.|2009|1317|doi:10.1002/ejoc.200801248
CCDC 1406085: Experimental Crystal Structure Determination
2016
Related Article: Tiina Saloranta, Anssi Peuronen, Johannes M. Dieterich, Janne Ruokolainen, Manu Lahtinen, Reko Leino|2016|Cryst.Growth Des.|16|655|doi:10.1021/acs.cgd.5b01135
CCDC 929860: Experimental Crystal Structure Determination
2013
Related Article: Denys Mavrynsky, Jani Rahkila, Daniel Bandarra, Soraia Martins, Margarida Meireles, Maria José Calhorda, Ida J. Kovács, István Zupkó, Mikko M. Hänninen, and Reko Leino|2013|Organometallics|32|3012|doi:10.1021/om400234p
CCDC 1956436: Experimental Crystal Structure Determination
2020
Related Article: Ida Mattsson, Ruzal Sitdikov, Andreas C. M. Gunell, Manu Lahtinen, Tiina Saloranta-Simell, Reko Leino|2020|RSC Advances|10|3960|doi:10.1039/C9RA10378C
CCDC 1822427: Experimental Crystal Structure Determination
2018
Related Article: Ida Mattsson, Manu Lahtinen, Anssi Peuronen, Abhijit Sau, Andreas Gunell, Tiina Saloranta-Simell, Reko Leino|2018|Cryst.Growth Des.|18|3151|doi:10.1021/acs.cgd.8b00263
CCDC 1822426: Experimental Crystal Structure Determination
2018
Related Article: Ida Mattsson, Manu Lahtinen, Anssi Peuronen, Abhijit Sau, Andreas Gunell, Tiina Saloranta-Simell, Reko Leino|2018|Cryst.Growth Des.|18|3151|doi:10.1021/acs.cgd.8b00263
CCDC 929859: Experimental Crystal Structure Determination
2013
Related Article: Denys Mavrynsky, Jani Rahkila, Daniel Bandarra, Soraia Martins, Margarida Meireles, Maria José Calhorda, Ida J. Kovács, István Zupkó, Mikko M. Hänninen, and Reko Leino|2013|Organometallics|32|3012|doi:10.1021/om400234p
CCDC 798985: Experimental Crystal Structure Determination
2017
Related Article: Denys Mavrynsky, Liisa T. Kanerva, Reijo Sillanpää, and Reko Leino|2011|Pure Appl.Chem.|83|479|doi:10.1351/PAC-CON-10-09-05
CCDC 1825936: Experimental Crystal Structure Determination
2018
Related Article: Ida Mattsson, Manu Lahtinen, Anssi Peuronen, Abhijit Sau, Andreas Gunell, Tiina Saloranta-Simell, Reko Leino|2018|Cryst.Growth Des.|18|3151|doi:10.1021/acs.cgd.8b00263