1) "Reiterative chiral resolution/racemization/recycle (RRR synthesis) for an effective and scalable process for the enantioselective synthesis of a dual IDO1/TDO2 inhibitor imidazoisoindole derivative" Cristina Crescenzi, Thomas Fuchss, Dimitri Ippoliti, Annunziata Langella, Antonia Di Mola, Antonio Massa, Diego Rozzi Org. Proc. Res. Dev. 2020, 24, 1018-1023, doi.org/10.1021/acs.oprd.0c00004
2) "On the necessity of one-pot tautomer trapping in asymmetric Michael reactions of arylideneisoxazol-5-ones." Antonio Macchia, Valentina Dafnae Cuomo, Antonia Di Mola, Giovanni Pierri, Consiglia Tedesco, Laura Palombi, Antonio Massa Eur. J. Org. Chem. 2020, 2020, 2264-2270, doi.org/10.1002/ejoc.202000286
3) "An effective method for the determination of the enantio-purity of L-α-glycerophosphocholine (L-α-GPC)" Lorenzo de Ferra, Antonio Massa, Antonia Di Mola, Bernd Diehl, J. Pharm. Biomed. Anal. 2020, 183, 113152 doi.org/10.1016/j.jpba.2020.113152
4) "Synthesis of 2-Acetylbenzonitriles and Their Reactivity in Tandem Reactions with Carbon and Hetero Nucleophiles: Easy Access to 3,3-Disubstituted Isoindolinones" Antonia Di Mola, Miriam Di Martino, Vito Capaccio, Giovanni Pierri, Laura Palombi, Consiglia Tedesco, Antonio Massa Eur. J. Org. Chem. 2018, 1699–1708, doi.org/10.1002/ejoc.201800240
5) "Bifunctional Phase Transfer Catalysis in the Asymmetric Synthesis of Biologically Active Isoindolinones". A. Di Mola, M. Tiffner, F. Scorzelli, L. Palombi, R. Filosa, P. De Caprariis, M. Waser, A. Massa Beilstein J. Org. Chem. 2015, 11, 2591-2599 doi:10.3762/bjoc.11.279
6) Antonio MASSA | Publications (unisa.it)
1. Italian patent n°. MI 99/A 001529 del 13/07/1999: “Complessi a base di Titanio nella sintesi di poliesteri” (Titanium complexes in Polyester synthesis). S. Contessa, F. Francalanci, A. Massa.
2. Italian patent Ital. (2017), IT 1429728 B1 20170831. "Isoindolinoni, procedimenti per la produzione di loro derivati chirali e impiego di questi ultimi" (Isoindolinones, methods for the production of chiral derivatives and their applications) A. Massa, A. Di Mola, P. De Caprariis.
3. PCT Int. Appl. (2016), WO 2016178140 A1 20161110, Massa, Antonio; Di Mola, Antonia; De Caprariis, Paolo
4. European Patent EP 3292102 del 09.08.2021 - Enantioselective synthesis of isoindolinones. A. Massa, A. Di Mola, P. De Caprariis
Bracco Imaging S.p.A., during the XII Forum of "Borsa della Ricerca Awards 2021" has chosen to award 4AChem S.r.l.
"Borsa della Ricerca" is an Italian initiative designed to foster contact between the world of university research (groups, departments, spin offs), startups, companies, incubators and investors (public and private), through an original interaction format, able to concretely favor technological transfer and economic support for research.
Through innovative online and offline tools, meetings and projects that exploit original formats as well as networking and content sharing, all participants to the annual event can come into contact and collaborate in the dissemination of best practices and the circulation of innovative ideas.
1) "Reiterative chiral resolution/racemization/recycle (RRR synthesis) for an effective and scalable process for the enantioselective synthesis of a dual IDO1/TDO2 inhibitor imidazoisoindole derivative" Cristina Crescenzi, Thomas Fuchss, Dimitri Ippoliti, Annunziata Langella, Antonia Di Mola, Antonio Massa, Diego Rozzi Org. Proc. Res. Dev. 2020, 24, 1018-1023, doi.org/10.1021/acs.oprd.0c00004
ABSTRACT: Herein, we report an effective and scalable highly enantioselective synthesis of an 5H-imidazo[5,1-a]isoindole
derivative via an RRR-synthesis approach (resolution−racemization−recycle). Chiral resolution performed with the aid of 2,3-
dibenzoyl-D-tartaric acid allowed the obtaining of the desired enantiomer in high enantiopurity (>99% ee) and good yield. The
undesired enantiomer was subjected to racemization under basic conditions and again to resolution, improving the efficiency of the
entire process. The asymmetric formation of the new stereocenter in an early stage of the synthesis scheme was also investigated by
means of organocatalytic systems.
KEYWORDS: anticancer, heterocycles, 5H-imidazo[5,1-a]isoindole, asymmetric synthesis, chiral resolution
2) "On the necessity of one-pot tautomer trapping in asymmetric Michael reactions of arylideneisoxazol-5-ones." Antonio Macchia, Valentina Dafnae Cuomo, Antonia Di Mola, Giovanni Pierri, Consiglia Tedesco, Laura Palombi, Antonio Massa Eur. J. Org. Chem. 2020, 2020, 2264-2270, doi.org/10.1002/ejoc.202000286
Abstract: Herein we report the first asymmetric Michael reaction of arylidene-isoxazol-5-one with 1,3-diesters. Despite complex tautomer equilibria of the obtained Michael adducts, the one-pot entrapping strategy by the aid of different electrophiles/protecting groups led to the selective isolation of diverse N-substituted isoxazol-5-ones in very high overall yield and good enantioselectivity. Asymmetric three components Michael/electrophilic tautomer-entrapping and four-component Knoevenagel/Michael/electrophilic-tautomer-entrapping methodologies have also been developed. The enantiopurity of several final products was further increased after crystallization, up to > 99.9:0.1 er in good overall yields.
