Conference: Synthesis of versatile synthetic intermediates through copper catalysis
,

Current position

  • 12/2017 to present: Associate Professor Universidad Autónoma de Madrid, Spain
  • 01/2011 to 12/2014: Assistant Professor (Ramón y Cajal contract) Universidad Autónoma de Madrid, Spain

 

Education and Research Experience

  • 03/2008-12/2010: Institute of Organic Chemistry (CSIC), Madrid,Spain, Research Associate (Juan de la Cierva fellow) with Professor Roberto Fernández de la Pradilla
  • 03/2005-03/2008: Scripps Florida, FL, USA, Postdoctoral Associate with Professor William R. Roush
  • 06/1999-01/2005: Institute of Organic Chemistry (CSIC), Madrid, Spain, Ph.D. in Organic Chemistry with Professor Roberto Fernández de la Pradilla
  • 08/2001-12/2001: Ohio State University, OH, USA, Visiting student with Professor Robert S. Coleman
  • 06/1999: Bachelor’s degree in Chemistry

 

Fellowships and Awards

  • Thieme Journal Award 2015
  • Eli Lilly Young Researcher Award (Spain) 2014
  • Spanish Royal Society of Chemistry- Young Investigator Award 2014
  • ERC Starting Grant (2013, starting 02/2014)
  • JSP Fellowship 48th Bürgenstock Conference 2013
  • 2011-2017 Ramón y Cajal Contract
  • 2008-2010 Juan de la Cierva Contract (Research Associate)
  • 2005-2007 Postdoctoral Fellowship (Spanish government)
  • 2001-2005 Predoctoral Fellowship (Spanish government)
  • 2004 Eli Lilly Ph.D. award
  • 1999 UAM Bachelor’s Award (for the top students in Chemistry)
  • 1997-2000 Fellowship from the Madrid Regional Government

 

Publication list

44.  Parra, A.; Tortosa, M.* “Strained boronates do the trick”, Nat. Chem. 2019, 11, 104-106.
43.  Amenos, L.; Trulli, L.; Novoa, L.; Parra, A.; Tortosa, M.* “Stereospecific Synthesis of a-Hydroxy-Cyclopropylboronates from allylic epoxides”, Angew. Chem. Int. Ed. 2019, 58, https://doi.org/10.1002/anie.201812836.
42.  Guisan-Ceinos, M.; Martin-Heras, V.; Soler-Yanes, R.; Cardenas D. J.; Tortosa, M. “Copper-Catalysed Cross-Coupling of Alkyl Grignard Reagents and Propargylic Ammonium salts: Stereospecific Synthesis of Allenes”, Chem. Commun. 2018, 54, 8343.
41.  Martin-Heras, V.; Parra, A.; Tortosa, M.* “Cyclopropyl and Cyclobutylboronates and Silanes: A Stereoselective Approach”, Synthesis 2018, 50, 470-484 (invited review).
40.  López, A.; Clark, T.; Parra, A.*; Tortosa, M.* “Copper-Catalyzed Enantioselective Synthesis of b-Boron b-Amino Esters”, Org. Lett. 2017, 19, 6272-6275. (Highlighted in Synfacts 2018, 14, 0273).
39.  Jarava-Barrera. C.; Parra, A.; Amenós, L.; Arroyo, A.; Tortosa, M.* “Stereoselective Traceless Borylation-Allenation of Propargylic Epoxides: Dual Role of the Copper-Catalyst”, Chem. Eur. J. 2017, 23, 17478-17481. (Highlighted in Synfacts 2018, 14, 0169 and in https://www.organicchemistry.org/Highlights/2018/17September.shtm).
38.  Guisan-Ceinos, M.; Martin-Heras, V.; Tortosa M* “Regio- and Stereospecific Copper-Catalyzed
Reactions of Propargylic Ammonium Salts and Aryl Grignard Reagents”, J. Am. Chem. Soc. 2017, 139, 8448-8451. (Highlighted in https://www.organic-chemistry.org/abstracts/lit5/899.shtm).
37.  Guisan-Ceinos, M.; Parra, A.; Martin-Heras V.; Tortosa M.* “Enantioselective Synthesis of Cyclobutylboronates via a Copper-Catalyzed Desymmetrization Approach”, Angew. Chem. Int. Ed. 2016, 55, 6969-6972.
36.  Nair, R. M.; Mishra, J. K.; Li F.; Tortosa, M.; Yang, C.; Doherty, J. R.; Cameron, M.; Cleveland, J. L.; Roush, W. R.; Bannister, T. D. “Exploiting the co-reliance of tumors upon transport of amino acids and lactate: Gln and Tyr conjugates of MCT1 inhibitors”, Med. Chem. Commun. 2016, 7, 900-905.
35.  Jarava-Barrera, C.; Parra, A.; López, A.; Cruz-Acosta, F.; Collado-Sanz, D.; Cárdenas, D. J.; Tortosa
M.* “Copper-Catalyzed Borylative Aromatization of p‑Quinone Methides: Enantioselective Synthesis of Dibenzylic Boronates”. ACS Cat. 2016, 6, 442-446. (Highlighted in Synfacts 2016, 12, 291).
34.  Lopez, A.; Parra, A.; Jarava-Barrera, C.; Tortosa, M*. “Copper-Catalyzed Silylation of p-Quinone Methides: New Entry to Dibenzylic Silanes”. ChemComm 2015, 51, 17684-17687.
33.  Parra, A.; Tortosa, M*. “para-Quinone Methide: a New Player in Asymmetric Catalysis”. ChemCatChem 2015, 7, 1524-1526.
32.  Parra, A.; López, A.; Díaz-Tendero, S.; Amenós, L.; Garcia-Ruano, J. L.; Tortosa, M*. “Insight into
the Copper-Catalyzed Borylation of Strained Alkenes”, Synlett 2015, 26, 494. Invitation for the “Young Investigators Issue” 2015
31.  Parra, A.; Amenós, L.; Guisan-Ceinos M.; López, A.; Garcia-Ruano, J. L.; Tortosa, M*. “Coppercatalyzed
diastereo- and enantioselective desymmetrization of cyclopropenes: synthesis of cyclopropylboronates”. J. Am. Chem. Soc. 2014, 136, 15833-15836.
30.  Martín-Castro, M.; Tortosa, M. “Claisen Rearrangements” Comprehensive Organic Synthesis, 2nd Ed., Vol. 5.; Fürstner, A., Ed.; Elsevier, 2014.
29.  Doherty, J.; Yang, C.; Scott, K. E. N.; Cameron M. D.; Fallai, M.; Li, W.; Hall, M.; Amelio, A. L.; Mishra, J.; Li, F.; Tortosa, M.; Genau, H. M.; Rounbehler, R. J.; Lu, Y.; Dang, C. V.; Kumar, K. G.; Butler, A.; Bannister, T.; Hooper, A. T.; Unsal-Kacmaz, K.; Roush, W.; Cleveland, J. “Blocking Lactate Export by Inhibiting the Myc Target MCT1 Disables Glycolysis and Glutathione Synthesis”, Cancer Research 2014, 74, 908.
28.  Fraile, A.; Parra, A.; Tortosa, M.; Alemán, J. “Alkynals, Alkynones, Propiolates and Electron-Deficient Alkynes in Organocatalysis”. Tetrahedron 2014, 70, 9145.
27.  Alemán, J.; Tortosa, M. “From C-C to C-Heteroatom Bond Formation”, Stereoselective Organocatalysis, Vol. 5. Rios, R., Ed.; Wiley 2013.
26.  Alfaro, R; Parra, A.; Alemán, J.; Tortosa, M.* “New Methods in Organic Synthesis via Copper-Catalyzed Borylation Reactions: Stereoselective Synthesis of 1,4-Diols and Vinylboronates” Synlett 2013, 24, 0884-0812. Invited account
25.  Alfaro, R; Parra, A.; Alemán, J.; Garcia Ruano, J. L.; Tortosa, M.* “Copper(I)-Catalyzed Formal
Carboboration of Alkynes: Synthesis of Tri- and Tetrasubstituted Vinylboronates” J. Am. Chem. Soc.
2012, 134, 15165-15168. Highlighted in http://www.organicchemistry.org/abstracts/lit3/792.shtm.
24.  García Ruano, J. L.; Alemán, J.; Marzo, L.; Alvarado, C.; Tortosa, M.; Díaz-Tendero, S.; Fraile, A. “Expanding the Scope of Arylsulfonylacetylenes as Alkynylating Reagents and Mechanistic Insights in the Formation of Csp2Csp and Csp3Csp Bonds from Organolithiums” Chem. Eur. J. 2012, 18, 8414-8422.
23.  García Ruano, J. L.; Alemán, J.; Marzo, L.; Alvarado, C.; Tortosa, M.; Díaz-Tendero, S.; Fraile, A. “Arylsulfonylacetylenes as Alkynylating Reagents of Csp2-H Bonds Activated with Lithium Bases” Angew. Chem. Int. Ed. 2012, 51, 2712-2716.
22.  Tortosa, M* “Synthesis of Syn and Anti 1,4-Diols by Copper Catalyzed Boration of Allylic Epoxides” Angew. Chem. Int. Ed. 2011, 50, 3950-3953. Highlighted in Synform 2011, 08.
21.  Viso, A.; Fernández de la Pradilla, R.; Tortosa, M; García, A.; Flores, A. “α,β-Diamino Acids: Biological Significance and Synthetic Approaches” Chem. Rev., 2011,111, PR1-PR42.
20.  Alonso, D.; Vázquez, H.; Gamo, A.; Martínez-Esperón, F.; Tortosa, M.; Viso, A.; Fernández de la Pradilla, R.; Junquera, E.; Aicart, E.; Martín-Fontecha, M.; Benhamú, B.; López-Rodríguez, M. L.; Ortega-Gutiérrez, S. “Development of Fluorescent Ligands for the Human 5-HT1A Receptor”. ACS Med. Chem. Lett. 2010, 1, 249–253.
19.  Fernández de la Pradilla, R.;* Tortosa, M.;* Castellanos, E.; Viso, A.; Baile, R. “Sulfoxide-Directed Intramolecular [4+2] Cycloadditions of 2-Sulfinyl Butadienes” J. Org. Chem. 2010, 75, 1517-1533.
18.  Fernández de la Pradilla, R.; Montero, C.; Tortosa, M; Viso, A. “Asymmetric Claisen Rearrangements on Chiral Vinyl Sulfoxides” Chem. Eur. J. 2009, 15, 697-709.
17.  Tortosa, M.; Yakelis, N. A.; Roush, W. R. “Total Synthesis of (+)-Superstolide A” J. Org. Chem. 2008, 73, 9657-9667.
16.  Fernández de la Pradilla, R.; Lwoff, N.; del Águila, M. A.; Tortosa, M.; Viso, A. “[2,3]-Sigmatropic Rearrangement of 3-Sulfinyl Dihydropyrans: Application to the Syntheses of the Cores of ent-Dysiherbaine and Deoximalayamicin A” J. Org. Chem. 2008, 73, 8929-8941.
15.  Fernández de la Pradilla, R.;Tortosa, M.; Lwoff, N.; del Águila, M. A.; Viso, A. “Sulfur-Directed Enantioselective Synthesis of Functionalized Dihydropyrans” J. Org. Chem. 2008, 73, 6716-6727
14.  Tortosa, M.; Yakelis, N. A.; Roush, W. R. “Total Synthesis of (+)-Superstolide A” J. Am. Chem. Soc. 2008, 130, 2722-2723. Highlighted in Synfacts 2008, 786.
13.  Fernández de la Pradilla, R.; Tortosa, M.; Viso, A. “Sulfur Participation in [3,3]-Sigmatropic Rearrangements” Topics in Current Chemistry 2007, 275, 103-129.
12.  Viso, A.; Fernández de la Pradilla, R.; Flores, A.; García, A.; Tortosa, M.; López-Rodríguez, M. L. “Synthesis of Highly Substituted Enantiopure Piperazines and Ketopiperazines from Vicinal NSulfinyl Diamines” J. Org. Chem. 2006, 71, 1442-1448.
11.  Fernández de la Pradilla, R.; Tortosa, M. “Base-Induced Enantioselective Synthesis of Sulfinyl Dihydropyrans” Phosphorus, Sulfur, and Silicon and the Related Elements 2005, 180, 1217-1222
10.  Viso, A.; Fernández de la Pradilla, R.; García, A.; Guerrero-Strachan, C.; Alonso, M.; Tortosa, M.; Flores, A.; Lwoff, N.; López-Rodríguez, M. L.; Martínez-Ripoll, M.; Fonseca, I.; André, I.; Rodríguez, A. “Highly Diastereoselective [3+2] Cycloadditions between Non-racemic p-Tolylsulfinimines and Iminoesters: an Efficient Entry to Enantiopure Imidazolidines and Vicinal Diaminoalcohols” Phosphorus, Sulfur, and Silicon and the Related Elements 2005, 180, 1229-1234.
9.  Fernández de la Pradilla, R.; Viso, A.; Montero, C.; Tortosa, M. “Highly Diastereoselective Diels-Alder with Enantiopure Sulfinyl-substituted 1-Hydroxymethyldienes” Chem. Eur. J. 2005, 11, 5136-5145.
8.  Fernández de la Pradilla, R.; Viso, A.; Castro, S.; Fernández, J.; Manzano, P.; Tortosa, M. “Sulfoxide-Controlled SN2′ Displacements between Cuprates and Vinyl and Alkynyl Epoxy Sulfoxides” Tetrahedron 2004, 60, 8171-8180.
7.  Fernández de la Pradilla, R.; Tortosa, M. “Sulfoxide-Directed Enantioselective Synthesis of Functionalized Dihydropyrans” Org. Lett. 2004, 6, 2157-2160.
6.  Fernández de la Pradilla, R.; Buergo, M. V.; Martínez, M. V.; Montero, C.; Tortosa, M.; Viso, A. “Sulfur-Directed Synthesis of Enantiopure Hydroxy 2-Sulfinyl Butadienes” J. Org. Chem. 2004, 69, 1542-1547.
5.  Fernández de la Pradilla, R.; Baile, R.; Tortosa, M. “Sulfoxide-Directed Thermal Intramolecular [4+2] Cycloadditions between 2-Sulfinyl Butadienes and Unactivated Alkynes” Chem. Commun. 2003, 2476-2477.
4.  Viso, A.; Fernández de la Pradilla, R.; García, A.; Guerrero-Strachan, C.; Alonso, M.; Tortosa, M.; Flores, A.; Martínez-Ripoll, M.; Fonseca, I.; André, I.; Rodríguez, A. “Highly Diastereoselective [3+2] Cycloadditions between Non-racemic p-Tolylsulfinimines and Iminoesters: an Efficient Entry to Enantiopure Imidazolidines and Vicinal Diaminoalcohols” Chem. Eur. J. 2003, 9, 2867-287.
3.  Fernández de la Pradilla, R.; Fernández, J.; Manzano, P.; Méndez, P.; Priego, J.; Tortosa, M.; Viso, A.; Martínez-Ripoll, M.; Rodríguez, A. “Nucleophilic Epoxidation of α’-Hydroxy Vinyl Sulfoxides” J. Org. Chem. 2002, 67, 8166-8177.
2.  Fernández de la Pradilla, R.; Montero, C.; Tortosa, M. “Sulfinyl-Mediated Chirality Transfer in Diastereoselective Claisen Rearrangements” Org. Lett. 2002, 4, 2373-2376.
1.  Viso, A.; Fernández de la Pradilla, R.; López-Rodríguez, M. L.; García A.; Tortosa, M. “Synthesis of Enantiopure 1-Benzyl-2,3-disubstituted Piperazines from Enantiopure p-Toluenesulfinimines” Synlett 2002, 755-758.

 

Invited Lectures

  • University of Basel, Basel, February 2019.
  • RSC Heterocyclic & Synthesis Group January Meeting 2019, The Institute of Cancer Research, London, January 2019.
  • University of Zurich, Zurich, December 2018.
  • VI Brazil-Spain Workshop on Organic Chemistry, Oviedo, October 2018.
  • GlaxoSmithKline, Stevenage, UK, June 2018.
  • University of Tokyo, Tokyo, May 2018.
  • Institute of Transformative Bio-Molecules, Nagoya, May 2018.
  • Osaka University, May 2018.
  • The Second Japanese-Spanish Symposium on Organic Synthesis, Tokyo, May 2018.
  • Girona Seminar 2018, Girona, Spain, April 2018.
  • ETH, Zurich, Switzerland, March 2018.
  • Novartis, Basel, Switzerland, March 2018.
  • Université Catholique de Louvain, Louvain La Neuve, Belgium, March 2018.
  • Instituto de Investigaciones Químicas, Sevilla, Spain, February 2018.
  • Barluenga Lectureship Symposium 2017, Oviedo, Spain, November 2017.
  • ICIQ School, Tarragona, Spain, 2017.
  • German-Spanish Symposium on Frontiers in Chemistry, Tarragona, Spain, 2017.
  • 11th International School of Organometallic Chemistry (ISOC), San Benedetto del Tronto, Italy, 2017.
  • 20th European Symposium on Organic Chemistry (ESOC), Cologne, Germany, 2017.
  • Centro de Investigación en Química Sostenible, Huelva, Spain, 2017.
  • CINQUIMA, Instituto Universitario, Valladolid, Spain, 2017.
  • Instituto universitario de bio-organica Antonio González, Tenerife, Spain 2017.
  • 6 Jornadas de la Red de Catálisis Asimétrica – Red CASI, Palma de Mallorca, Spain, 2016.
  • 9th Asian-European Symposium on Metal-Mediated Efficient Organic Synthesis (AES), Stockholm, Sweden, 2016.
  • EFMC International Symposium on Medicinal Chemistry (EFMC-ISMC), Manchester, UK, 2016.
  • 11th Spanish-Italian Symposium on Organic Chemistry SISOC-XI, San Sebastian, Spain, 2016.
  • Universidad de Zaragoza, Zaragoza, Spain, 2015.
  • 7th Spanish Portuguese Japanese Organic Chemistry Symposium, Sevilla, Spain, 2015.
  • Janssen Pharmaceuticals, Toledo, Spain, 2015.
  • New perspectives in asymmetric and organometallic synthesis 4th edition, Valencia, Spain, 2014.
  • XI Simposio de Investigadores Jóvenes, Bilbao, Spain, 2014.
  • Instituto de Química Orgánica General, CSIC, Madrid, Spain, 2014.
  • 6th EuCheMS Organic Division Young Investigators Workshop, Cyprus, 2014.
  • Eli Lilly, Award lecture, Alcobendas, Spain, 2014.
  • XXV Spanish Symposium on Organic Chemistry, Eli Lilly Award lecture, Alicante, Spain, 2014.
  • Institut Català d’Investigació Química (ICIQ), Tarragona, Spain, 2013.

 

Retour aux conférenciers