CURRICULUM VITTORIO PACE, PhD
Department of Drug and Natural Products Synthesis
Althanstrasse 14, A-1090 Vienna Austria Ernst Mach Postdoctoral Fellow Junior Professor of Organic Chemistry (“Habilitation” of the Spanish Ministry of Education, October 2010)EDUCATION: Complutense University of Madrid, Faculty of Chemical Sciences PhD in Chemistry (cum laude) Advisor: Professor Andrés Rafael Alcántara León Dissertation: Integrated Approach to the Synthesis and Reactivity of New α-Haloketones. University of Pavia (Italy), Faculty of Pharmacy M. Sc. in Drug Development and Design Advisor: Professor Marco Terreni Dissertation: The Versatility of the Use of Supported Potassium Fluoride in Phthalimide Chemistry: from N-Functionalization to Intramolecular Cyclization.
Complutense University of Madrid, Faculty of Chemical Sciences
Advisor: Professor Andrés Rafael Alcántara León
Dissertation:Chemoenzymatic Synthesis of Homoquiral Secondary University of Perugia (Italy), Faculty of Pharmacy Degree with first class honors in Pharmacy Advisor: Professor Massimo Curini; Dr. Ornelio Rosati Dissertation: Functionalization of Coumarin Derivatives: Synthesis of 3-Substituted 5-amino-1,10b-dihydro-2H-cromeno-[3,4-c]pyridine- 2,4-(3H)diones.
RESEARCH EXPERIENCE: University of Vienna (Austria), Pharmazie Zentrum, Dept. Drug and Natural Products Synthesis (Prof W. Holzer)
Applications of lithium carbenoids to the preparation of complex haloketones; Metallation of multifunctionalized electrophiles.
Ghent University (Belgium), Faculty of Bioscience Engineering, Dept. Organic Chemistry (Prof. N. De Kimpe) Synthesis of α-halo-α’-arylaminopropan-2-ones,
halomethyllithium chemistry and Arndt-Eistert synthesis.
Karl-Franzens University of Graz (Austria), Dept. Organic and Bioorganic Chemistry (Prof. W. Kroutil)
Enantioselective bioreductions of prochiral α-haloketones.
University of Trieste (Italy), Dept. Pharmaceutical Sciences (Prof. L. Gardossi)
Molecular Modeling studies on enantioselective prediction.
University of Perugia (Italy), Dept. Organic Chemistry (Prof. M. Curini) Synthesis of functionalized coumarins. (Diploma thesis) PUBLICATIONS:
1. Pace, V.; Sinisterra, J. V.; Alcántara, A. R.; Holzer, W. Versatile and Ecofriendly Protection/Deprotection of Anilines as N-tert-butyldimethylsilyl Derivatives.Green Chem. submitted, under review (Manuscript GC-COM-05-2011-000119).
2. Hoyos, P.; Pace, V.; Sinisterra, J. V.; Alcántara A. R. Chemoenzymatic Synthesis of Chiral Unsymmetrical Benzoin Esters.Adv. Synth. Cat.submitted, under review (Manuscript ID: adsc.201100281).
3. Pace,V.; Hoyos, P.; Sinisterra, J. V.; Alcántara, A. R.; Holzer, W. Highly Regioselective and Efficient Synthesis of Aminoepoxides by Ring Closure of Aminohalohydrins Mediated by KF/Celite. Synlett 2011accepted, in press (Manuscript DLMH72/3/11).
4. Pace, V.; Castoldi, L.; Hoyos, P.; Sinisterra, J. V.; Pregnolato, M.; Sánchez- Montero,
J. M. Highly Regioselective Control of 1,2 Addition of Organolithiums to Α,Β- Unsaturated Compounds Promoted by Lithium Bromide in 2-Methyltetrahydrofuran: A Facile and Green Access to Allylic Alcohols and amines. Tetrahedron 2011, 67, 2670.
5. Pace V.; Cortés A.; Ferrario V.; Sinisterra J. V.; Ebert C.; Gardossi L.; Braiuca P.;
Alcántara A. R. Structural Bases for Understanding the Stereoselectivity for Ketones Bioreductions Performed by ADH from Thermus thermophilus: A Quantitative Model. J. Mol. Catal. B: Enzym. 2011, 70, 23.
6. Pace V. 1,3-dichloroacetone. Synlett 2010, 2825.
7. Pace V.; Cortés C. A.; Fernández, M.; Sinisterra, J. V.; Alcántara, A. R. First general synthetic route to substituted α-chloro-α’-arylaminopropan-2-ones by Oxidation of Corresponding N-protected Aminohalohydrins: The Importance of Disrupting H-bond Networks. Synthesis 2010, 3545.
8. Pace V.; Hoyos, P.; Fernández, M.; Sinisterra, J. V.; Alcántara, A. R. 2-Methyltetrahydrofuran as a Suitable Green Solvent for Phthalimide Functionalization Promoted by Supported KF. Green Chem.,2010, 12, 1380.
9. Pace V.; Verniest G.; Sinisterra J. V.; Alcántara A. R.; De Kimpe N. Improved Arndt-Eistert Synthesis of α-Diazoketones Requiring Minimal Diazomethane in the Presence of Calcium Oxide as Acid Scavenger. J. Org. Chem. 2010, 75, 5760.
10. Pace V.; Sinisterra J. V.; Alcántara A. R. Celite-Supported Reagents in Organic Synthesis: An Overview. Curr. Org. Chem. 2010, 14, 2384.
11. Pace V.; Martínez F.; Fernández M.; Sinisterra J. V.; Alcántara Andrés R. Highly Efficient Synthesis of New a-Arylamino-a'-Chloropropan-2-Ones Via Oxidative Hydrolysis of Vinyl Chlorides Promoted by Calcium Hypochlorite. Adv. Synth. Cat. 2009, 351, 3199-3206.
12. Pace V.; Martínez F.; Fernández M.; Nova C. I.; Sinisterra J. V.; Alcántara A. R.
Efficient Horner-Wadsworth-Emmons Intramolecular Cyclisation of a N-Substituted Phthalimide Promoted by KF-Alumina: A General Tool for the Synthesis of Functionalized Isoindolinones. Tetrahedron Letters 2009, 50, 3050-3053.
13. Pace V.; Sinisterra J. V.; Alcántara A. R. Potassium Fluoride-Celite. Encyclopedia of Reagents for Organic Synthesis;John Wiley & Sons Ltd., 2009, www.mrw.interscience.wiley.com/eros/, DOI: 10.1002/047084289X.rp216.pub2.
14. Pace V.; Martinez F.; Fernández M., Sinisterra J. V., Alcantara A. R. Effective Monoallylation of Anilines Catalyzed by Supported KF. Org. Lett. 2007, 9, 2661-2664.
15. Curini M.; Rosati O.; Marcotullio M. C.; Montanari F.; Campagna V.; Pace V.;
Cravotto G. Preparation of 2-Amino-4H-Chromene Derivatives from Coumarins in Basic Media. Eur. J. Org. Chem. 2006, 746-751. MANUSCRIPTS IN PREPARATION:
Pace V., Verniest G., Holzer, W., Alcántara A. R., De Kimpe N. Synthesis of Widely Functionalized a-arylamino-a'-Chloropropan-2-onesvia Chloromethyllithium Carbenoids (to be submitted);
Pace, V.; Verniest, G.; Holzer, W., Alcántara A. R., De Kimpe N. Synthesis and Functionalisation of a-arylamino- a'-diazoacetones through an Improveed Arndt- Eistert Pathway (to be submitted);
Pace, V.; Holzer, W. Regioselective Metallation of 2-Haloacrylate Derivatives: Efficient Synthesis of Heteroaromatic Allylic Alcohols Not Accessible through Baylis-Hillman Chemistry (to be submitted);
Pace, V.; Hoyos, P.; Sinisterra, J. V.; Alcántara A. R. Simple and Efficient Synthesis of Oxazolidinone Chemoterapics Starting From Epichlorohydrins (in preparation);
Pace, V.; Alcántara, A. R.; Holzer, W. On the Instability of a-arylamino-a'-chloropropan-2-ones in Acidic and Photochemical Conditions (in preparation);
Pace, V.; Verniest, G.; Holzer, W., Alcántara A. R., De Kimpe N. Alkylation of Arylamines through 1,3-dihalopropanones Derivatives: an Easy and Direct Access to Privileged Haloketones (in preparation);
Pace, V.; Hoyos, P.; Holzer, W., Alcántara A. R. Reductive Amination of halopyruvate derivatives for the Synthesis of Aminoketones.
Pace, V.; Hoyos, P.; Mutti, F.; Sinisterra, J.V.; Kroutil, W.; Alcántara A. R.
Stereoselective Bioreductions of New α-Haloketones Performed by Employing Alcohol Dehydrogenase from Thermus thermophilus (in preparation);
Hoyos, P.; Pace, V.; Sinisterra, J. V., Alcántara A. R. Dynamic Kinetic Resolution via Enzyme-Metal Combo Catalysis in Stereoselective Synthesis of Bioactive Compounds Stereoselective Synthesis of Drugs and Natural Products (Andrushko, V.; Andrushko, N. Eds); Wiley (invitedbook chapter, in preparation);
Pace, V.; Hoyos, P.; Domínguez de María, P.; Sinisterra, J. V.; Alcántara, A. R. 2-methyltetrahydrofuran: a green alternative to THF (review article, in preparation). ORAL COMMUNICATIONS:
1. Pace, V. Improved Use of an Old Reagent: how to Use Minimal Diazomethane Amounts
(VII Young Researchers Symposium, November 2010, Valencia, Spain).
2. Pace, V. α-Arylamino-α’-Halomethylketones in Organic Synthesis: Synthetic Routes and Applications (XIV Ischia Advanced School of Organic Chemistry, September 2010, Ischia, Italy).
3. Pace, V. The First Oxidative Rearrangement of Arylamino Vinyl Halides for an Expeditious Synthesis of Privileged α-Haloketones (Organic Chemistry Summer School, June 2009, Gargnano, Italy).
4. Pace, V. Highly Efficient Synthesis of New a-Arylamino-a'-Chloropropan-2-Ones Via Oxidative Hydrolysis of Vinyl Chlorides Promoted by Calcium Hypochlorite (7th Spanish-Italian Symposium in Organic Chemistry, September 2008, Oviedo, Spain).
POSTER PRESENTATIONS:
1. Pace, V.; Sinisterra, J. V.; Alcántara, A. R. XIV Ischia Advanced School of Organic Chemistry. Ischia (Italy) September 2010. α-Arylamino-α’-Halomethylketones in Organic Synthesis: Synthetic Routes and Applications.
2. Pace, V.; Sinisterra, J. V. ; Alcántara, A. R. 18th International Conference in Organic Synthesis. Bergen (Norway) August 2010. Highly Functionalized α-Haloketones: Synthetic Protocols and Applications in Organic Synthesis.
3. Pace, V.; Verniest, G.; Sinisterra, J. V.; Alcántara, A. R.; De Kimpe, N. XIII Sigma Aldrich Belgian Young Chemists Symposium. Spa (Belgium). December 2009. Use of Vinyl Halides as Masked α-Haloketones: The First Synthesis of α-arylamino-α’-haloketones.
4. Pace, V.; Sinisterra, J. V., Alcántara, A. R. 21th International Symposium: Synthesis in Organic Chemistry. Oxford (UK). July 2009. Oxidative Hydrolysis of Vinyl Halides As A Versatile Approach To The Synthesis of New α-Haloketones.
5. Pace, V.; Cortés-Cabrera Á.; Ferrario, V.; Gardossi, L.; Ebert, C.; Sinisterra, J. V.;
Braiuca, P.; Alcántara, A. R. 9th International Symposium Biotrans 2009. Bern (Switzerland). July 2009. Molecular Modelling of asymmetric bioreductions of ketones with ADH from Thermus thermophilus for obtaining new enantiopure halohydrins.
6. Pace, V.; Martínez, F.; Fernández, M.; Sinisterra, J. V.; Alcántara, A. R. V Sigma Aldrich Spanish Young Chemists Symposium. Santiago de Compostela (Spain).
November 2008. Non-Racemic Halohydrins via Vinyl Chloride Oxidation and Biocatalytic Hydrogen Transfer of α-Haloketones.
7. Pace, V.; Martínez, F.; Fernández, M.; Sinisterra, J. V.; Alcántara, A. R. V Sigma Aldrich Spanish Young Chemists Symposium. Santiago de Compostela (Spain). November 2008. N-alkylation of Cyclic Imides Promoted by Potassium Fluoride coated on Alumina.
8. Pace, V.; Martínez, F.; Fernández, M.; Sinisterra, J. V.; Alcántara, A. R. 8th International Symposium Biotrans 2007. Oviedo (Spain). Chemoenzymatic synthesis of homochiral building blocks for drug preparation via whole cells catalyzed reaction.PARTICIPATION IN RESEARCH PROJECTS:
1. Solvsafe (Advanced Safer Solvents for Innovative Industrial Eco-Processing).EU Project (ref. FP6-2003-NMP-SME-3). Director Prof. J. V. Sinisterra (January 2006-March 2009);
2. Chemioenzymatic Síntesis of Linezolid. Spanish Ministry of Research Project (ref. CIT-
320100_2005-39). Director Prof. A. R. Alcántara (January 2006-June 2006);
3. ENZTEREDOX: Redox Processes catalyzed by Termophilic Microorganisms.Madrid Regional Council Project (ref. REF. S-0505/PPQ/0344). Director Prof. J. V. Sinisterra (January 2006-December 2009);
4. Coupling of Dynamic Kinetic Resolution of Secondary Alcohols with Enzymatic Alkene Cleavage to Obtain Valuable Acyloins. Spanish-Austrian Scientific Cooperation (ref. 2007-0023). Director Prof. J. V. Sinisterra (January 2008-June 2010);
5. Chemoenzymatic Síntesis of Glicomimetics.Spanish Ministry of Research Project (ref.
CTQ-2009-11801). Director Prof. M. J. Hernáiz (January 2009-December 2012).
TEACHING EXPERIENCE
Assistant in laboratory courses of Organic Chemistry I and Organic Chemistry II at the
Universities of Madrid and Vienna (2007-present);
Assistant in examinations of Organic Chemistry I and Organic Chemistry II at the
Alumni supervised during their own Diploma theses: Laura Castoldi, Álvaro Cortés-
Cabrera, David Muñoz Solano, Valeria Fieni (University of Madrid).
FURTHER REMARKS:
Universitary Teacher’s Training Fellowship (Beca del Programa Nacional de
Formación de Profesorado Universitario, ref. AP2005-5112) 01.04.2006 – 31.03.2010;
Spanish Mother Tongue Level (Diploma de Español como Lengua Extranjera –
Nivel Superior). Spanish Ministry of Education. November 2006;
Honorary Collaborator of the Organic and Pharmaceutical Chemistry Department –
Complutense University. October 2007-September 2009;
Scientific Collaborator of Abbott. Laboratories Madrid for NMR analysis of drug
formulations (March 2009-September 2009).
REFERENCES: Prof. Dr. Wolfgang Holzer (actual Postdoctoral supervisor)
University of Wien, Department of Drug and Natural Products Synthesis
Tel. +43-1-4277-55623; [email protected]Prof. Dr. Andrés Rafael Alcántara León (PhD advisor)
Pza. Ramón y Cajal s/n, 28040 Madrid, Spain
Complutense University of Madrid, Faculty of Pharmacy, Department of Organic and Pharmaceutical Chemistry
Tel. +34-91-3941820; [email protected]
Coupure Links 653, B-9000 Ghent, Belgium
University of Ghent, Faculty of Bioscience Engineering, Department of Organic Chemistry
Tel. +32-09-264.59.51; [email protected]
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