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innCAT - Innovation in catalysis - Design and screening of modular ligand libraries for asymmetric catalysis
 
Publications 2014-2016
1. M. Magre, O. Pàmies,* M. Diéguez*
"PHOX-Based Phosphite-Oxazoline Ligands for the Enantioselective Ir-Catalyzed Hydrogenation of Cyclic ß-Enamides"
ACS Catalysis 2016, 6, 5186.

2. R. Bellini, M. Magre, M. Biosca, P.-O. Norrby,* Oscar Pàmies,* M. Diéguez,*, C. Moberg*
"Conformational Preferences of a Tropos Biphenyl Phosphinooxazoline-a Ligand with Wide Substrate Scope"
ACS Catalysis 2016, 6, 1701.

3. J. Margalef, M. Coll, P.-O. Norrby,* O. Pàmies,* M. Diéguez,*
" Asymmetric Catalyzed Allylic Substitution Using a Pd/P-S Catalyst Library with Exceptional High Substrate and Nucleophile Versatility: DFT and Pd-p-allyl Key Intermediates Studies
Organometallics 2016, DOI: 10.1021/acs.organomet.6b00547

4. O. Pàmies,* M. Diéguez*
"Adaptable P–X Biaryl Phosphite/Phosphoroamidite-Containing Ligands for Asymmetric Hydrogenation and C–X Bond-Forming Reactions: Ligand Libraries with ExceptionallyWide Substrate Scope"
Chemical Record 2016, DOI: 10.1002/tcr.201600062. Invited review. Special issue commemorating the 15th anniversary of the Nobel Prize in Chemistry to Professor Noyori

5. O. Pàmies,* M. Magre, M. Diéguez*
"Extending the Substrate Scope for the Asymmetric Iridium-Catalyzed Hydrogenation ofMinimally Functionalized Olefins by Using Biaryl Phosphite-Based Modular Ligand Libraries"
Chemical Record 2016, 16, 1578. Invited review

6. J. Margalef, O. Pàmies, M. Diéguez*
"Designing new readily available sugar-based ligands for asymmetric transfer hydrogenation of ketones. In the guest to expand the substrate scope"
Tetrahedron Letters 2016, 57, 1301. Invited digest article

7. M. Biosca, M. Coll, E. Manoury*, R. Poli, Pàmies, M. Diéguez*
"Ferrocene-based phosphine-thioether ligands for Ir-catalyzed hydrogenation of minimally functionalized olefins"
Tetrahedron 2016, 72, 2623. Invited paper for the Special issue Chiral Sulfur Ligands in Asymmetric Catalysis.

8. Magre, M.; Biosca, M.; Pàmies, O.; Diéguez, M.
Filling the Gaps in the Challenging Asymmetric Hydroboration of 1,1-Disubstituted Alkenes with Simple Phosphite-Based Phosphinooxazoline Iridium Catalysts
ChemCatChem 2015, 7, 114. Selected for front cover

9. Pàmies, O.; Diéguez, M.; Bäckvall, J.-E.
Artificial metalloenzymes in asymmetric catalysis: Key developments and future directions
Advanced Synthesis & Catalysis 2015, 357, 1567. Invited review for the special issue ASC in Biocatalysis. Selected as VIP article and for front cover.

10. Orgue, S.; Flores-Gaspar, A.; Biosca, M.; Pàmies, O.; Diéguez, M.; Riera, A.; Verdaguer, X.
Stereospecific SN2@P reactions: novel access to bulky P-stereogenic ligands
Chemmical Communications 2015, 51, 17548

11. Magre, M.; Biosca, M.; Norrby, P.-O.; Pàmies, O.; Diéguez, M.
Theoretical and experimental optimization of a new amino phosphite ligand library for asymmetric palladium-catalyzed allylic substitution
ChemCatChem 2015, 7, 4091

12. Biosca, M.; Paptchikhine, A.; Pàmies, O.; Andersson, P.G.; Diéguez, M.
Extending the Substrate Scope of Bicyclic P-Oxazoline/Thiazole Ligands for Ir-Catalyzed Hydrogenation of Unfunctionalized Olefins by Introducing a Biaryl Phosphoroamidite Group
Chemistry-A European Journal 2015, 21, 3455

13. Borrás, C.; Biosca, M.; Pàmies, O.; Diéguez, M.
Iridium-Catalyzed Asymmetric Hydrogenation with Simple Cyclohexane-Based PS Ligands: In Situ HP-NMR and DFT Calculations for the Characterization of Reaction Intermediates
Organometallics 2015, 34, 5321

14.Verendel, J.J.; Pàmies, O.; Diéguez, M.; Andersson, P.G.
Asymmetric hydrogenation of Olefins using chiral crabtree-type catalysts-scope and limitations
Chemical Reviews 2014, 114, 2130

15. Alegre, S.; Alberico, E.; Pàmies, O.; Diéguez, M.
Rh-catalyzed asymmetric hydrogenation using a furanoside monophosphite second-generation ligand library: scope and limitations
Tetrahedron: Asymmetry 2014, 25, 258. Highlighted in Synfacts 2014, 511

16. Alegre, S.; Matta, Y.; Pàmies, O.; Diéguez, M.
Asymmetric Pd-catalyzed allylic substitution using a large sugar-based monophosphite ligand library. Scope and limitations
Asymmetric Catalysis 2014, 1, 32. Invited paper

17. Coll, M.; Pàmies, O.; Diéguez, M.
Modular hydroxyamide and thioamide pyranoside-based ligand library from the sugar pool: new class of ligands for asymmetric transfer hydrogenation of ketones
Advanced Synthesis & Catalysis 2014, 356, 2293

18. Margalef, J.; Caldenty, X.; Karlsson, E.A.; Coll, M.; Mazuela, J.; Pàmies, O.; Diéguez, M.; Pericàs, M.A.
A Theoretically-Guided Optimization of a New Family of Modular P,S-Ligands for Iridium-Catalyzed Hydrogenation of Minimally Functionalized Olefins
Chemistry-A European Journal 2014, 20, 12201

19. Coll, M.; Mazuela, J.; Pàmies, O.; Diéguez, M.
Highly versatile Pd-thioether-phosphite catalytic systems for asymmetric allylic alkylation, amination, and etherification reactions
Organic Letters 2014, 16, 1892. Highlighted in Synfacts 2014, 729

Publications 2009-2013

1. Raluy, E.; Pàmies, O.; Diéguez, M.
“Modular furanoside phosphite-phosphoroamidites, a readily available ligand library for asymmetric palladium-catalyzed allylic substitution reactions. Origin of enantioselectivity”
Advanced Synthesis and Catalysis. 2009, 351, 1648.


2. Raluy, E.; Pàmies, O.; Diéguez, M.
“Furanoside phosphite–phosphoroamidite: new ligand class for the asymmetric nickel-catalyzed trialkylaluminium addition to aldehydes”
Tetrahedron Letters. 2009, 50, 4495.
3. Raluy, E.; Pàmies, O.; Diéguez, M.; Rosset, S.; Alexakis, A.
“Furanoside phosphite–phosphoroamidite and diphosphoroamidite ligandsfor Cu-catalyzed asymmetric 1,4-addition reactions”
Tetrahedron: Asymmetry. 2009, 20, 1930.
4. Raluy, E.; Pàmies, O.; Diéguez, M.; Rosset, S.; Alexakis, A.
“Sugar-based phosphite and phosphoroamidite ligands for the Cu-catalyzed asymmetric 1,4-addition to enones”
Tetrahedron: Asymmetry. 2009, 20, 2167
5. Raluy, E.; Pàmies, O.; Diéguez, M.
“Screening of a modular sugar-based phosphoramidite ligand library in the asymmetric nickel-catalyzed trialkylaluminum addition to aromatic aldehydes”
Tetrahedron: Asymmetry. 2009, 20, 1575
6. Mazuela, J.; Coll, M.; Pàmies, O.; Diéguez, M.
“Rh-Catalyzed Asymmetric Hydroformylation of Heterocyclic Olefins Using Chiral Diphosphite Ligands. Scope and Limitations”
Journal of Organic Chemistry. 2009, 74, 5440
7. Mazuela, J.; Verendel, J.J.; Coll, M.; Schäffner, B.; Börner, A.; Andersson, P.G.; Pàmies, O.; Diéguez, M.
“Iridium phosphite-oxazoline catalysts for the highly enantioselective hydrogenation of terminal Alkenes”
Journal of the American Chemical Society. 2009, 131, 12344.
8. Rivas, A. B.; Pérez-Torrente, J. J.; Pardey, A. J.; Masdeu-Bultó, A. M.; Diéguez, M.; Oro, L. A.
“Hydroformylation of oct-1-ene catalyzed by dinuclear gem-dithiolato-bridged rhodium(I) complexes and phosphorus donor ligands”
Journal of Molecular Catalysis A: Chemical. 2009, 300, 121.
9. Mata, Y.; Pàmies, O.; Diéguez, M.
“Pyranoside phosphite-oxazoline ligand library: Highly efficient modular P-N ligands for Pd-catalyzed allylic substitution reactions. A study of the key Pd-p-allyl intermediates”
Advanced Synthesis and Catalysis. 2009, 351, 3217.
10. Diéguez, M.; Pàmies, O.
“Biaryl phosphites: New efficient adaptative ligands for Pd-catalysed asymmetric allylic substitution reactions”
Accounts of Chemical Research. 2010, 43, 312.
11. Mazuela, J.; Paptchikhine, A.; Tolstoy, P.; Pàmies, O.; Diéguez, M.; Andersson, P. G.
“A new class of modular P,N-ligand library for asymmetric Pd-catalyzed allylic substitution reactions. A study of the key Pd-p-allyl intermediates”
Chemistry-A European Journal. 2010, 16, 620.
12. Mazuela, J.; Pàmies, O.; Diéguez, M.
“Biaryl phosphite-oxazolines from the chiral pool: Highly efficient modular ligands for the asymmetric Pd-catalyzed Heck reaction”
Chemistry-A European Journal. 2010, 16, 3434.
13. Mazuela, J. ; Pàmies, O. ; Diéguez, M. ; Palais, L. ; Rosset, S. ; Alexakis, A.
“Fine-tunable monodentate phosphoroamidite and aminophosphine ligands for Rh-catalyzed asymmetric hydroformylation”
Tetrahedron: Asymmetry. 2010, 21, 2153.
14. Mazuela, J.; Paptchikhine, A.; Pàmies, O.; Andersson, P.G.; Diéguez, M.
“Adaptative Biaryl Phosphite-Oxazole and Phosphite-Thiazole Ligands for Asymmetric Ir-Catalyzed Hydrogenation of Alkenes”
Chemistry-A European Journal. 2010, 16, 4567.
15. Diéguez, M.; Pàmies, O.; Woodward, S.
“Use of sugar-based ligands in selective catalysis. Recent developments”
Coordination Chemistry Reviews. 2010, 254, 2007. Review.
16. Pàmies,O.; Andersson,P.G.; Diéguez,M.
“Asymmetric Hydrogenation of Minimally Functionalised Terminal Olefins: An Alternative Sustainable and Direct Strategy for Preparing Enantioenriched Hydrocarbons”
Chemistry-A European Journal. 2010, 16, 14232. Review.
17. Van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Claver, C.; Pàmies, O.; Dieguez, M.
“Phosphite-containing ligands for asymmetric catalysis”
Chemical Reviews. 2011, 111, 2077. Review.
18. Mazuela, J.; Tolstoy, P.; Pàmies, O.; Andersson, P.G.; Diéguez, M.
“Phosphite-oxazole/imidazole ligands in asymmetric intermolecular Heck reaction”
Organic & Biomolecular Chemistry. 2011, 9, 941.
19. Gual,A.; Castillón, S.; Pàmies,O.; Diéguez,M.; Claver,C.
“C1-Symmetric carbohydrate diphosphite ligands for asymmetric Pd-allylic alkylation reactions. Study of the key Pd-allyl intermediastes”
Dalton Transactions. 2011, 40, 2852.
20. Alegre,S.; Pàmies,O.; Diéguez,M.
“Sugar-monophosphite ligands applied to the asymmetric Ni-catalyzed trialkylaluminum addition to aldehydes”
Tetrahedron-Asymmetry. 2011, 22, 834.
21. Coll, M.; Pàmies,O.; Diéguez, M.
“Thioether-phosphites: new ligands for the highly enantioselective Ir-catalyzed hydrogenation of minimally funtionalized olefins”
Chemical Communications. 2011, 47, 9215.
22. Mazuela, J.; Norrby, P-O.; Andersson, P.G.; Pàmies, O.; Diéguez, M.
Pyranoside Phosphite-Oxazoline Ligands for the Highly Versatile and Enantioselective Ir-Catalyzed Hydrogenation of Minimally Functionalized Olefins. A Combined Theoretical and Experimental Study Journal of the American Chemical Society. 2011, 133, 13634
23. Coll, M.; Pàmies, O.; Adolfsson, H.; Diéguez, M.
“Carbohydrate-based pseudo-dipeptides: New ligands for the highly enantioselective Ru-catalyzed transfer hydrogenation reaction”
Chemical Communications. 2011, 47, 12188.
24. Coll, M.; Pàmies, O.; Diéguez, M.
“Asymmetric Rh-catalyzed hydrogenation using a furanoside phosphite-phosphoroamidite and diphosphoroamidite ligand library”
Dalton Transactions. 2012, 41, 3038.
25. Magre, M.; Mazuela, J.; Diéguez, M. ; Pàmies, O. ; Alexakis, A.
“Furanoside phosphite-phosphoroamidite and diphosphoroamidite ligands applied to asymmetric Cu-catalyzed allylic substitution reactions”
Tetrahedron: Asymmetry. 2012, 23, 67.
26. Diéguez, M.; Pàmies, O.
“Asymmetric Intermolecular Mizoroki-Heck reaction: from phosphine/phosphinite-nitrogen to phosphite-nitrogen ligands”
Israel Journal of Chemistry. 2012, 7, 572, Invitation in Special Issue: Concepts in Asymmetric Catalysis
27. Coll, M.; Ahlford, K.; Pàmies, O.; Adolfsson, H.; Diéguez, M.
“Modular furanoside pseudo-dipeptides and thioamides, readily available ligand libraries for metal-catalyzed transfer hydrogenation reactions. Scope and limitations”
Advanced Synthesis and Catalysis. 2012, 354, 415.
28. Margalef, J.; Lega, M.; Ruffo, F.; Pàmies, O.; Diéguez, M.
“Application of pyranoside phosphite-pyridine ligands to enantioselective Ir-catalyzed hydrogenation of highly unfunctionalized olefins”
Tetrahedron: Asymmetry. 2012, 23, 945
29. Mazuela, J.; Pàmies, O.; Diéguez, M.
“Phosphite-Thiazoline versus Phosphite-Oxazoline for Pd-Catalyzed Allylic Substitution Reactions: A Case for Comparison”
ChemCatChem. 2013, 5, 1504.
30. Mazuela, J.; Pàmies, O.; Diéguez, M.
“Expanded scope of the asymmetric hydrogenation of minimally functionalized olefins catalyzed by iridium complexes with phosphite-thiazoline ligands”
ChemCatChem. 2013, 5, 2410.
31. Mazuela, J.; Pàmies, O.; Diéguez, M.
“A New Modular Phosphite-Pyridine Ligand Library for Asymmetric Pd-Catalyzed Allylic Substitution Reactions: A Study of the Key Pd-?-Allyl Intermediates”
Chemistry-A European Journal. 2013, 19, 2416.
32. Mazuela, J.; Pàmies, O.; Diéguez, M.
“Enantioselective Ir-catalyzed hydrogenation of minimally functionalized olefins using pyranoside phosphinite-oxazoline ligands”
European Journal of Inorganic Chemistry. 2013, 12, 2139.
33. Mazuela, J.; Pàmies, O.; Diéguez, M.
“A phosphite-pyridine/iridium complex ligand library as highly selective catalysts for the hydrogenation of minimally functionalized olefins”
Advanced Synthesis & Catalysis. 2013, 355, 2569.
34. Coll, M.; Pàmies, O.; Diéguez, M.
“A modular furanoside thioether-phosphite/phosphinite/phosphine ligand library for asymmetric iridium-catalyzed hydrogenation of minimally functionalized olefins: Scope and limitations”
Advanced Synthesis & Catalysis. 2013, 355, 143.
35. Coll, M.; Pàmies, O.; Diéguez, M.
“Second-generation amino acid furanoside based ligands from D-glucose for the asymmetric transfer hydrogenation of ketones”
Chemcatchem. 2013, 5, 3821.
36. Lega, M.; Margalef, J.; Ruffo, F.; Pàmies, O.; Diéguez, M.
“Application of pyranoside phosphite-pyridine ligands to enantioselective metal-catalyzed allylic substitutions and conjugate 1,4-additons”
Tetrahedron: Asymmetry. 2013, 24, 995.

Other representative publications

1. Diéguez, M.; Pàmies, O.; Ruiz, A.; Castillón, S.; Claver, C. “Chiral diphosphites derived from D-glucose: New ligands for the asymmetric catalytic hydroformylation of vinyl arenes” Chem. Eur. J. 2001, 7, 3086-3094.


2. Pàmies, O.; Bäckvall, J. E. “Combination of Enzymes and Metal Catalysts. A Powerful Approach in Asymmetric Catalysis” Chem. Rev. 2003, 103, 3247-3261.
3. Diéguez, M.; Pàmies, O.; Claver, C. “Ligands Derived from Carbohydrates for Asymmetric Catalysis” Chem. Rev. 2004, 104, 3189.
4. Pàmies, O.; Diéguez, M.; Claver, C. “New phosphite-oxazoline ligands for efficient Pd-catalyzed substitution reactions” J. Am. Chem. Soc. 2005, 127, 3646.
5. Diéguez, M.; Pàmies, O.; Claver, C. “First successful application of diphosphite ligands in the asymmetric hydroformylation of dihydrofurans” Chem. Commun. 2005, 1221-1223.
6. Mata, Y.; Diéguez, M.; Pàmies, O.; Woodward, S. “Screening of a Modular Sugar-Based Phosphite Ligand Library in the Asymmetric Nickel-Catalyzed Trialkylaluminum Addition to Aldehydes” J. Org. Chem. 2006, 71, 8159-8165.
7. Mata, Y..;Pàmies, O.; Diéguez, M. “Screening of a modular sugar-based phosphite-oxazoline ligand library in asymmetric Pd-catalyzed Heck reactions” Chem. Eur. J. 2007, 13, 3296-3304.
8. Pàmies, O.; Diéguez, M. “Screening of a phosphite-phosphoroamidite ligand library for palladium-catalyzed asymmetric allylic substitution reactions: the origin of enantioselectivity” Chem. Eur. J. 2008, 14, 944-960.
9. Diéguez,. M.; Pàmies, O. “Modular phosphite-oxazoline/oxazine ligand library for asymmetric Pd-catalyzed allylic substitution reactions: scope and limitations-origin of enantioselectivity” Chem. Eur. J. 2008, 14, 3653-3669.
10.- Alexakis, A.; Bäckvall, J.-E.; Krause, N.; Pàmies, O.; Diéguez, M. “Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions” Chem. Rev. 2008, 108, 2796.
11. Diéguez, M.; Pàmies, O.; Mata, Y.; Teuma, E.; Gómez, M.; Ribaudo, F.; van Leeuwen, P.W.N.M. “Palladium nanoparticles in allylic alkylation and Heck reactions: the molecular nature of the catalyst studied in a membrane reactor” Adv. Synth. Cat. 2008, 350, 2583-2598.
12. Diéguez, M.; Mazuela, J.; Pàmies, O.; Verendel, J. J.; Andersson, P. G. “Chiral pyranoside phosphite-oxazolines: a new class of ligand for asymmetric catalytic hydrogenation of alkenes” J. Am. Chem. Soc. 2008, 130, 7208.

 

Universitat Rovira i Virgili

Departament de Física i Química Inorgànica

 

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