Dipartimento di Scienze Chimiche e Geologiche

EDUCATION:

2006 Phd in Synthetic Organic Chemistry. University of Cagliari (Italy) / Universite` Paris-Sud XI Orsay (France). Strained Carbocyclic Systems in the Synthesis of Bioactive Compounds. Methodology and Total Synthesis. (Supervisors: Professor Pier Paolo Piras (University of Cagliari) and Dr. Jean Ollivier (Universite` Paris-Sud XI, Orsay).

2002 MSc in Chimica e Tecnologie Farmaceutiche (Medicinal Chemistry). University of Cagliari (Italy). Final mark: 110/110 with honour. New approaches at the Synthesis of (±)-Grandisol and (±)-Fragranol Using Cyclopropane Derivatives. (Supervisor: Professor Pier Paolo Piras).

Specific knowledge: High experience in theoretical and practical knowledge of the organic synthetic methods (extensive experience in: carbo- and heterocyclic synthesis. Synthesis and transformation of strained carbocyclic systems (cyclopropanes and –butanones). Total synthesis. Homogeneous asymmetric organo-catalytic synthesis. Extensive experience in enantioselective organometallic synthesis and organolithium/diamine enantioselective deprotonations of N-heterocycles and phosphorous compounds. Enantioselective synthesis and functionalization of sulphur compounds. Enantioselective synthesis of P-stereogenic ligands and P-stereogenic-Phosphorous-Nitrogen ligands .

 

WORK EXPERIENCE:

01/10/2012-present. Research associate ,Dipartimento di scienze Chimiche e Geologiche. Former researcher at the Università degli Studi di Cagliari, research subjects: Development of new synthetic organo- and metallo-catalyzed green methodologies. Enantioselective synthesis of highly functionalized carbo- and heterocyclic building blocks and bioactive compounds.

05/2007-05/2010 post doctoral researcher, Department of Chemistry, University of York, York, UK/Celtic-catalysts ltd. Dublin, Novacenter UCD Dublin, Ireland. Research subject: Enantioselective synthesis of P-stereogenic ligands. Enantioselective deprotonation of prochiral Phosphine-borane, -sulphide and -oxides with organolithium bases/(-)-sparteine and (+)-sparteine surrogate complexes. Supervisors: Professor Peter O`Brien (university of York, Professor Declan Gilheany and Dr. Brian Kelly, CelticCatalysts Ltd.). Marie Curie fellowship T.O.K. (name of the project: PHOSCOM).

03/2006-03/2007 post doctoral fellow, University of Cagliari, Dipartimento di Scienze Chimiche funding by C.I.N.M.P.I.S. inter-universitary consortium. Research subject: enantio- and stereoselective synthesis of cyclobutanone derivatives and their application for the synthesis of bioactive molecules.

2003-2006 chemistry research activity, University of Cagliari, Dipartimento di Scienze Chimiche/ ICMMO, CNRS, Universite` Paris-Sud XI, funding by Ministry of instruction, University and Research (MIUR) for PhD thesis preparation.

2000-2002 chemistry research activity, University of Cagliari, Dipartimento di Scienze Chimiche (supervisor: Professor Pier Paolo Piras)/ ICMMO, CNRS, Universite` Paris-Sud XI, (supervisor: Dr. Jaques Salaun, research Director, CNRS-France) for the preparation of the diploma (laurea) dissertation.

 

Teaching From 2012 , Organic Chemistry lecturer for the Ist and IInd year students Msc in Material Sciences-Chemistry.

From 2014, Organic Chemistry lecturer for the Ind year students Msc in Biotechnology Sciences

From 2015, Organic Chemistry lecturer for the IInd year students Msc in Medicinal Chemistry (CTF)

 

STATE COMPETITIVE EXAMINATIONS:

2010 winner of the research project F.I.R.B. funded by MIUR (2011-2013) grant n. RBFR083M5N_002

2009 winner of a fellowship funded by Università degli Studi di Cagliari/MIUR

2007 winner of a funded by Marie Curie Foundation fellowship-T.O.K (2007-2009)

2006 winner of a fellowship funded by C.I.N.M.P.I.S 2006-2007.

2002 winner of a fellowship funded by M.I.U.R. for 2003-2006

 

COURSES AND CONFERENCES ATTENDED:

2002 SardiniaChem, University of Cagliari, Cittadella Universitaria di Monserrato (CA), June 2002 (poster presentation).

2003 XXI Convegno della Societa` Chimica Italiana S.C.I. Torino, June, 22nd-27th 2003 (poster presentation).

2003 Seminari di Sintesi Organica, XXVIII Corso estivo di Chimica Organica A. Corbella, Gargnano, June, 16th-20th 2003

Deuxiemme Ecolle Doctorale de Chimie de l`Universite` Paris-sud, Campus scientifique d`Orsay, july, 2005 (oral presentation)

2005 Seminari di Sintesi Organica, XXX Corso estivo di Chimica Organica A. Corbella, Gargnano, June, 13th-17th 2005 (oral presentation)

2006 SardiniaChem, University of Cagliari, Cittadella Universitaria di Monserrato (CA), June 2006 (oral presentation).

2006 II Scuola estiva nazionale Chiralita` Molecolare: Origine, Riconoscimento e applicazioni, Dipartimento di Chimica, Università` di Perugia, Perugia, July 3rd-6th 2006.

2006 6th SAYCS, Sigma Aldrich Young Chemists Symposium, Riccione, October, 9th-11th 2006 (oral presentation).

2008 Sheffield Stereochemistry Meeting, (Modern aspects of Stereochemistry) University of Sheffield, 15th January, 2008.

2008  Ninth anglo-Norman Organic Chemistry Colloquium, Le Havre (Haute-Normandie), 3rd-5th April 2008 (poster presentation).

2008 University Research Conference, Chemistry Department, University of York, York, 16th September 2008 (oral presentation).

2009 Sheffield Stereochemistry Meeting, (Modern aspects of Stereochemistry) University of Sheffield, 13th January, 2009.

2009 Royal Chemical Society of Chemistry, North Eastern Regional Organic Chemistry Meeting, University of Leeds, Scohol of chemistry, April, 1st 2009.

2009 Università degli Studi di Sassari, Parola ai Giovani, june 30

2009 WorSar, workshop Regionale Sardo degli Assegnasti di Ricerca, september 24-25. Monserrato (Ca)

2010 ISOCS-24 24th international Symposium on the Organic Chemistry of Sulfur, Firenze, July 25-30

2010 XXXIII Convegno Nazionale della Divisione di Chimica Organica della Società Chimica Italiana, San Benedetto del Tronto (AP), September 12-16

2012 BIT’s 3rd Annual World Congress of Catalytic Asymmetric Synthesis 2012. Beijing China. Invited speaker. Asymmetric Enantioselective Transformation of Cyclobutanone Derivatives. Beijing China, 12-14 May 2012.

2013 XXXV Convegno Nazionale della Divisione di Chimica Organica della Società Chimica Italiana, Sassari (SS), september 9-13.

2014 BOS2014 Balticum Organicum Syntheticum BOS-chem. July 6-9, Vilnius (Lithuania).

2014 C.I.N.M.P.I.S. Ventennium Conference 1994-2014. Invited speaker, Bari (Ba) september 29-30

 

Articles on international journals

1) Synthesis of new heterocycles through a cation-driven tandem ring-enlargement – Annulation reaction Bernard, A.M., Cadoni, E., Frongia, A., Piras, P.P., Secci, F. Organic Letters 2002, 4, 2565-2567

2) Unexpected stereochemistry in the lithium salt catalyzed ring expansion of nonracemic oxaspiropentanes. Formal syntheses of (-)-(4R,5R)-muricatacin and the pheromone (R)-japonilure Bernard, A.M., Frongia, A., Piras, P.P., Secci, F. Organic Letters 2003, 5, 2923-2926.

3) Stereospecific palladium(0)-catalyzed reduction of 2-cyclobutylidenepropyl esters. A versatile preparation of diastereomeric monoterpenoids: (±)-fragranol and (±)-grandisol Bernard, A.M., Frongia, A., Secci, F., Delogu, G., Ollivier, J., Piras, P.P., Salaün, J. Tetrahedron 2003, 59, 9433-9440.

4) Use of cyclobutyl derivatives as intermediates in the synthesis of 1,2a,3,8b-tetrahydro-2H-cyclobuta[c]chromenes Bernard, A.M., Floris, C., Frongia, A., Piras, P.P., Secci, F. Tetrahedron 2004, 60, 449-457.

5) A new synthesis of alkylidenecyclopropanes by the Julia-Lythgoe-type olefination using sulfones and sulfoxides Bernard, A.M., Frongia, A., Piras, P.P., Secci, F. Synlett 2004, 6,1064-1068.

6) 2,2-Dimethyl cyclopentanones by acid catalyzed ring expansion of isopropenylcyclobutanols. A short synthesis of (±)-?-cuparenone and (±)-herbertene Bernard, A.M., Frongia, A., Secci, F., Piras, P.P. Chem. Commun., 2005, 30, 3853-3855.

7) Regioselective synthesis of trisubstituted 2,3-dihydrofurans from donor-acceptor cyclopropanes or from reaction of the corey ylide with ?-sulfenyl-, ?-sulfinyl-, or ?-sulfonylenones Bernard, A.M., Frongia, A., Piras, P.P., Secci, F., Spiga, M. Org. Lett., 2005, 7, 4565-4568.

8) Intramolecular capture of a cyclobutylthionium ion for the synthesis of new strained heterocycles and carbocycles: A rapid assembly of the BCD ring sequence of penitrems Alberti, G., Bernard, A.M., Frongia, A., Piras, P.P., Secci, F., Spiga, M. Synlett, 2006, 14, 2241-2245.

9) L-proline-catalyzed direct intermolecular asymmetric aldol reactions of 1-phenylthiocycloalkyl carboxaldehydes with ketones. Easy access to spiro-and fused-10) cyclobutyl tetrahydrofurans and cyclopentanones Bernard, A.M., Frongia, A., Guillot, R., Piras, P.P., Secci, F., Spiga, M. Org. Lett. 2007, 9, 541-544.

10) Convenient formal synthesis of (±)-cuparene, (±)-enokipodins A and B, and (±)-cuparene-1,4-quinone Secci, F., Frongia, A., Ollivier, J., Piras, P.P. Synthesis 2007, 7, 999-1002.

11) A highly stereocontrolled formal total synthesis of (±)- and of (-)-grandisol by 1,4-conjugated addition of organocopper reagents to cyclobutylidene derivatives Bernard, A.M., Frongia, A., Ollivier, J., Piras, P.P., Secci, F., Spiga, M. Tetrahedron 2007, 63, 4968-4974.

12) Oxaspiropentane derivatives as effective sex pheromone analogues in the gypsy moth: Electrophysiological and behavioral evidence Solari, P., Crnjarr, R., Frongia, A., Sollai, G., Secci, F., Spiga, M., Masala, C., Liscia, A. Chemical Senses 2007, 32, 755-763.

13) Synthesis of enantiomerically enriched secondary and tertiary phenylthio- and phenoxy-aldols Bernard, A.M., Frongia, A., Piras, P.P., Secci, F., Spiga, M. Tetrahedron: Letters, 2008, 49, 3037-3041.

14) Convenient formal synthesis of (+)-grandisol through Lewis acid promoted enantioselective pinacolic rearrangement Frongia, A., Girard, C., Ollivier, J., Piras, P.P., Secci, F. Synlett 2008, 18, 2823-2825.

15) Easy access to trans-2,3-disubstituted cyclobutanones, 2,4,5-trisubstituted 3,6-dihydro-2H-pyrans and cis-substituted phenylcyclopropylsulfones by using the highly versatile 1-phenylsulfenyl- or 1-phenylsulfonyl-cyclopropylketones Alberti, G., Bernard, A.M., Floris, C., Frongia, A., Piras, P.P., Secci, F., Spiga, M. Org. Biomol. Chem., 2009, 7, 3512-3519.

16) Kinetic resolution of P-stereogenic phosphine boranes via deprotonation using s-butyllithium/(-)-sparteine Granander, J., Secci, F., O’Brien, P., Kelly, B. Tetrahedron: Asymmetry, 2009, 20, 2432-2434.

17) Enantioselective organocatalytic rearrangement of ?-acyloxy- ?-keto sulfides to ?-acyloxy thioesters Capitta, F., Frongia, A., Piras, P.P., Pitzanti, P., Secci, F. Adv. Synth. Catal. 2010, 352, 2955-2960.

18) Unexpected formation of optically active 4-substituted 5-hydroxy-?- lactams by organocatalyzed reaction of 3-substituted cyclobutanones with nitrosobenzene Capitta, F., Frongia, A., Ollivier, J., Piras, P.P., Secci, F. Synlett, 2011, 1, 89-93.

19) The first organocatalysed direct aldol reaction of 2-hydroxycyclobutanone Aitken, D.J., Capitta, F., Frongia, A., Gori, D., Guillot, R., Ollivier, J., Piras, P.P., Secci, F., Spiga, M. Synlett, 2011, 5, 712-716.

20) One-ligand catalytic asymmetric deprotonation of a phosphine borane: Synthesis of P-stereogenic bisphosphine ligands. Granander, J., Secci, F., Canipa, S.J., O’Brien, P., Kelly, B. J. Org. Chem., 2011, 76, 4794-4799.

21) Organocatalytic Asymmetric Tandem Condensation-Intramolecular Rearrangement-Protonation: An Approach to Optically Active a-Amino Thioester Derivatives Capitta, F., Frongia, A., Piras, P. P., Pitzanti P., Secci, F. Org. Biomol. Chem., 2012, 10, 490-494.

22) Enantioselective organocatalyzed functionalization of benzothiophene and thiophenecarbaldehyde derivatives Secci, F., Cadoni, E., Fattuoni, C., Frongia A., Bruno, G., Nicolò, F. Tetrahedron, 2012, 68, 4773-4781.

23) Solvent-free stereoselective organocatalyzed aldol reaction of 2-hydroxycyclobutanone. Aitken, D.J., Capitta, F., Frongia, A., Ollivier, J., Piras, P.P., Secci, F. Synlett, 2012, 23, 727-730.

24) Very high stereoselectivity in organocatalyzed desymmetrizing aldol reactions of 3-substituted cyclobutanones. David J. Aitken, Angela M. Bernard, Francesca Capitta, Angelo Frongia, Régis Guillot, Jean Ollivier, Pier Paolo Piras, Francesco Secci and Marco Spiga. Org. Biomol. Chem., 2012, 10, 5045-5048.

25) Catalytic Enantioselective Synthesis of ?-Arylamino Cyclobutanones. D. J. Aitken, P. Caboni, H. Eijsberg, A. Frongia, R. Guillot, J. Ollivier, P. P. Piras, F. Secci, Adv. Synth. Catal., 2014, 356, 941-945.

26) A pheromone analogue affects the evaporation rate of (+)-disparlure in Lymantria dispar

Sollai, G., Murgia, S., Secci, F., Frongia, A., Cerboneschi, A., Masala, C., Liscia, A., Solari, P. Pest Manag Sci, 2014, 70, 674-681.

27) Ammonium salt catalyzed oxidation of organosulfides to organosulfoxydes Secci, F., Frongia, A., Piras, P.P. Tetrahedron: Letters, 2014, 55, 603-605.

28) Catalytic enantioselective Amadori-Heyns rearrangement of racemic ?-hydroxy ketones with arylamines: Synthesis of optically active ?-arylamino ketones. Frongia, A., Secci, F., Capitta, F., Piras, P.P., Sanna, M.L. Chem. Commun., 2013, 49, 8812-8814.

29) Stereocontrolled synthesis and functionalization of cyclobutanes and cyclobutanones. Secci, F., Frongia, A., Piras, P.P. Molecules, 2013, 18, 15541-15572.

30) Photochemical transformation of a 1,2-dihydropyridin-3-one: An original tandem retro-[4+2]/[2+2] cycloaddition process. Aitken, D.J., Frongia, A., Gaucher, X., Ollivier, J., Rafique, H., Sambiagio, C., Secci, F. Tetrahedron: Letters, 2013, 54, 2825-2827.

31) Tetrazole amides as hydrogen-bonding donor catalysts in the chemoselective oxidation of sulphides and disulphides. F. Secci, M. Arca, A. Frongia and P. P. Piras. Catal. Sci. Technol., 2014, 4, 1407-1415.

32) Synthesis of P-Stereogenic Phospholene Boranes via Asymmetric Deprotonation and Ring-Closing Metathesis. W. Xiao, P. O’Brien, S. Ellwood, F. Secci, B. Kelly. Org. Lett., 2013, 15, 192-195.

33) From (Phenylsulfanyl)cycloalkanecarbaldehydes to Optically Active Spirocyclic Tetrahydrofurans: Stereospecific Resolution of Symmetric Aldehydes through (S)-Proline-Catalysed Aldol Reaction. F. Secci, A. Frongia, M. G. Rubanu, M. L. Sechi, G. Sarais, M. Arca, P. P. Piras, Eur. J. Org. Chem., 2014, 30, 6659-6675.

34) Organocatalytic Synthesis of Optically Active Arillactic Acid Derivatives from b-Ketosulfoxides. F. Capitta, N. Melis, F. Secci, G. Romanazzi, A. Frongia, J. Sulfur Chem., 2014, 649-660.

35) Organocatalytic Asymmetric Condensation/Keto-enol Tautomerization Tandem Reaction: Access to Cyclobutanone ?-Amino Acid Ester Derivatives. A Frongia, N. Melis, I. Serra, F. Secci, P. P. Piras, P. Caboni, Asian J. Org. Chem., 2014, 9, 1334-1340.

36) Synthesis and Caracterization of Tunable Coumarin-linked glasse sas a new class of organic/inorganic phosphors. A. Luridiana, G. Petta, F. Secci, A. Frongia, D. Chiriu, C. M. Carbonaro, R. Corpino, P. C. Ricci. Fundam. Applic. In Silica and Adv. Dielectr., 2014, 81-86.

37) Enantioselective Organocatalized Desymmetrization of 3-substituted Cyclobutanones through Michael Addition to Nitroalkenes. F. Capitta, A. Frongia, J. Ollivier, D.J. Aitken, F. Secci, Francesco, P. P. Piras, R. Guillot. 2015, DOI: 10.1055/s-0034-1379489; Art ID: st-2014-d0757-l.

38) New Aminotetrazole Derivatives as Hydrogen Bonding Catalysts. A green and Selective Oxidation of Organosulphides with H2O2 in H2O. F. Secci, M. Arca, A. Frongia P.P. Piras, New J. Chem., 2014, 38, 3622-3629.

39) Catalytic Enantioselective Synthesis of ?-Arylaminocyclobutanones. D. J. Aitken, P. Caboni, H. Eijsberg, A. Frongia, R. Guillot, J. Ollivier, P. P. Piras, F. Secci, Adv. Synth. Catal., 2014, 356, 941–945.

40) Organocatalyzed Tandem Process Involving asymmetric Protonations as a Stereodefining Step. Frongia, A. Melis, N. Secci, F. C.R. Chim. 2014, doi:10.1016/j.crci.2014.05.002.

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