Le Touquet – Paris-Plage, France
Le Touquet – Paris-Plage, France

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Rast S.,Slovenian National Institute of Chemistry | Modec B.,University of Ljubljana | Stephan M.,Slovenian National Institute of Chemistry | Stephan M.,PhosPhoenix SARL | Mohar B.,Slovenian National Institute of Chemistry
Organic and Biomolecular Chemistry | Year: 2016

The synthesis of new enantiopure syn- and anti-3-(α-aminobenzyl)-benzo-γ-sultam ligands 6 and their application in the ruthenium(ii)-catalyzed asymmetric transfer hydrogenation (ATH) of ketones using formic acid/triethylamine is described. In particular, benzo-fused cyclic ketones afforded excellent enantioselectivities in reasonable time employing a low loading of the syn ligand-containing catalyst. A never-before-seen dynamic kinetic resolution (DKR) during reduction of a γ-keto carboxylic ester (S7) derivative of 1-indanone is realized leading as well to excellent induction. © The Royal Society of Chemistry.


Stephan M.,Slovenian National Institute of Chemistry | Stephan M.,PhosPhoenix SARL | Modec B.,University of Ljubljana | Mohar B.,Slovenian National Institute of Chemistry
Tetrahedron Letters | Year: 2011

An efficient and high-yielding (up to 57% overall yield) asymmetric route to enantiopure P-stereogenic 1,2-bis[(o-hydroxyaryl)(phenyl)phosphino-P-borane] ethanes wherein aryl = phenyl and naphthyl, is presented. The occurring P-stereomutation is confirmed through X-ray crystal structure analysis of key intermediates. © 2011 Elsevier Ltd. All rights reserved.


Zupancic B.,Slovenian National Institute of Chemistry | Mohar B.,Slovenian National Institute of Chemistry | Stephan M.,Slovenian National Institute of Chemistry | Stephan M.,PhosPhoenix SARL
Organic Letters | Year: 2010

A series of R-SMS-Phos ligands was evaluated in the Rh(I)-catalyzed hydrogenation of a set of olefins showing a marked influence of the cyclic nature and structure of the R groups. Overall, cPen- and Cy-SMS-Phos performed efficiently, while Ph- and Bn-SMS-Phos exhibited slower kinetics and furnished lower ees also compared with C6F5CH2-SMS-Phos. The Rh(I)-(Cy-SMS-Phos) catalyst was screened under mild conditions displaying excellent enantioselectivities and high TOFs. Cases of catalysis under catalyst or substrate control were identified. © 2010 American Chemical Society.


Kisic A.,Slovenian National Institute of Chemistry | Stephan M.,Slovenian National Institute of Chemistry | Stephan M.,PhosPhoenix SARL | Mohar B.,Slovenian National Institute of Chemistry
Advanced Synthesis and Catalysis | Year: 2014

A diversified ansa-ruthenium(II) catalyst series 1b-f displaying enantiopure N,C-(N-alkylene-N-methylsulfamoyl)-tethered (DPEN-κ2N,N')/η6-arene (DPEN=trans-1,2-diphenylethylenediamine) hybrid ligands was screened in the transfer hydrogenation of alkyl aryl ketones, and α- or β-diketones in formic acid-triethylamine (HCO2H-Et3N) medium under mild conditions and furnished the alcohols in high to excellent ees. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Kisic A.,Slovenian National Institute of Chemistry | Stephan M.,Slovenian National Institute of Chemistry | Stephan M.,PhosPhoenix SARL | Mohar B.,Slovenian National Institute of Chemistry
Advanced Synthesis and Catalysis | Year: 2015

New 3rd generation designer ansa-ruthenium(II) complexes featuring N,C-alkylene-tethered N,N-dialkylsulfamoyl-DPEN/η6-arene ligands, exhibited good catalytic performance in the asymmetric transfer hydrogenation (ATH) of various classes of (het)aryl ketones in formic acid/triethylamine mixture. In particular, benzo-fused cyclic ketones furnished 98 to >99.9% ee using a low catalyst loading. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Mohar B.,Slovenian National Institute of Chemistry | Stephan M.,Slovenian National Institute of Chemistry | Stephan M.,PhosPhoenix SARL
Advanced Synthesis and Catalysis | Year: 2013

The rhodium(I)-{1,2-bis[(o-tert-butoxyphenyl)(phenyl)phosphino]ethane} [Rh(I)-(t-Bu-SMS-Phos)] catalyst system displayed prime efficiency in the hydrogenation of large series of aamidostyrenes and a-amidoacrylates. Up to >99.9% enantiomeric excesses coupled with very high reaction rates were attained operating routinely under 1-10 bar of hydrogen at 22 °C in methanol. Examples include industrial substrates. © 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.


Kisic A.,Slovenian National Institute of Chemistry | Stephan M.,Slovenian National Institute of Chemistry | Stephan M.,PhosPhoenix SARL | Mohar B.,Slovenian National Institute of Chemistry
Organic Letters | Year: 2013

The first second-generation designer Ru(II) catalyst 1b featuring an enantiopure N,C-(N-ethylene-N-methyl-sulfamoyl)-tethered (DPEN- κ2N,N′)/η6-toluene hybrid ligand is introduced. Using an S/C = 1000 in HCO2H-Et3N 5:2 transfer hydrogenation medium, secondary 1-naphthyl alcohols are obtained in up to >99.9% ee under mild conditions. Mechanistic factors are discussed. © 2013 American Chemical Society.


Stephan M.,Slovenian National Institute of Chemistry | Stephan M.,PhosPhoenix SARL | Sterk D.,Slovenian National Institute of Chemistry | Zupancic B.,Slovenian National Institute of Chemistry | Mohar B.,Slovenian National Institute of Chemistry
Organic and Biomolecular Chemistry | Year: 2011

A diversified family of enantiopure P-stereogenic "R-SMS-Phos" {R-SMS-Phos = 1,2-bis[(o-RO-phenyl)(phenyl)phosphino]ethane} ligands wherein R = branched or heteroatom-substituted alkyl, aralkyl, silyl, acyl, sulfonyl, etc. was screened for the Rh(i)-catalyzed hydrogenation of a representative set of olefinic substrates. This systematic and detailed investigation revealed a marked beneficial impact on enantioselectivity and catalyst activity in comparison to Knowles' ultimate DiPAMP {DiPAMP = 1,2-bis[(o-anisyl)(phenyl) phosphino]ethane} design. Mutant ligands with highly enhanced properties possessing particular features wherein the DiPAMP structure is found embedded were identified. © The Royal Society of Chemistry 2011.


Zupancic B.,Slovenian National Institute of Chemistry | Mohar B.,Slovenian National Institute of Chemistry | Stephan M.,Slovenian National Institute of Chemistry | Stephan M.,PhosPhoenix SARL
Organic Letters | Year: 2010

"Chemical Equation Presented" A serles of enantiopure P-stereogenic 1,2-bis[(o-RO-phenyl)(phenyl)phosphino]ethane (R-SMS-Phos) ligands wherein R= i-Pr, i-Bu, tf-Bu, 3-Pen, and CH2TMS was assessed in the Rh(l)-catalyzed hydrogenation of an indicative set of olefins. The best performing t-Bu-SMS-Phos ligand was screened against a wide range of representative classes of standard and new oleflnic substrates such as dehydroamldo esters, dehydro-aamido-phosphonates, enamides, itaconates, acrylates, enol acetates, α-phosphonovinyl benzoates, α-(2-pyridyl N-oxide)styrenes, and α-(1-hydroxyliminoethyl)styrenes, Excellent enantloselectivities and high TOFs were attained under mild conditions. © 2010 American Chemical society.


Rast S.,Slovenian National Institute of Chemistry | Stephan M.,Slovenian National Institute of Chemistry | Stephan M.,PhosPhoenix SARL | Mohar B.,Slovenian National Institute of Chemistry | Mohar B.,PhosPhoenix SARL
Tetrahedron Letters | Year: 2012

A series of sterically hindered o-(branched alkoxy)-tert-butoxybenzenes was efficiently prepared in good yields owing to a new practical and simple preparation of o-tert-butoxyphenol starting from catechol and isobutene. Use of DMF di-tert-butyl acetal reagent instead of isobutene/H 2SO 4 (cat.) for O-tert-butylation was very convenient in case of ortho bulky phenols affording the corresponding tert-butyl ethers in high yield and purity. This general route proved to be useful since no reliable access was available to o-di-t-BuO-substituted arenes. Application to the synthesis of congested phosphorus-based compounds is presented. © 2012 Elsevier Ltd. All rights reserved.

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