| dcterms.contributor.author | De Fusco, Claudia | |
| dc.date.accessioned | 2014-05-23T11:15:03Z | |
| dc.date.available | 2014-05-23T11:15:03Z | |
| dcterms.date.issued | 2013-01-30 | |
| dcterms.identifier.uri | http://hdl.handle.net/10556/1323 | |
| dcterms.identifier.uri | http://dx.doi.org/10.14273/unisa-201 | |
| dc.description | 2011 - 2012 | en_US |
| dc.description.abstract | This PhD work describes the development of different Michael and Michael type
processes employing different bifunctional organocatalysts. All the processes studied
involved a non-covalent activation of the substrates provided by the organic promoters.
An asymmetric epoxidation of electron-poor trisubstituted olefins has been developed by
employing the commercially available diphenyl prolinol which afforded the epoxides in
high yield, complete diastereocontrol and good enantioselectivity. Diaryl prolinols were
found to promote a Michael addition of -ketoesters to nitroalkenes. An unexpected high
efficiency and stereocontrol was observed with hexafluorobenzene as unconventional
solvent, but also employed as an additive. A convenient tandem double Michael addition
process was developed to access symmetrically and unsymmetrically 3,5-diaryl
substituted cyclohexanones by using quinine as catalyst. An aziridination reaction of
terminal electron-poor olefins has been disclosed by using a commercially available
aminothiourea catalyst. The desired aziridines, bearing a quaternary stereocenter, were
isolated in good yield and enantiocontrol. These compounds, were regioselectively ringopened to access valuable ,-disubstituted -amino ester derivatives. Finally an
asymmetric Fischer indolization to produce helical molecules was investigated employing
a chiral phosphoric acid as promoter and an ion-exchange polymer as ammonia
scavenger. [edited by Author] | en_US |
| dc.language.iso | en | en_US |
| dcterms.publisher.alternative | Universita degli studi di Salerno | en_US |
| dcterms.subject | Organocatalysis | en_US |
| dcterms.subject | Michael | en_US |
| dcterms.subject | Enantioselective | en_US |
| dcterms.title | Stereoselective carbon-carbon and carbon-heteroatom bond formation mediated by bifunctional organocatalysts | en_US |
| dcterms.type | Doctoral Thesis | en_US |
| dc.subject.miur | CHIM/06 CHIMICA ORGANICA | en_US |
| dc.contributor.coordinatore | Guerra, Gaetano | en_US |
| dc.description.ciclo | XI n.s. | en_US |
| dc.contributor.tutor | Lattanzi, Alessandra | en_US |
| dc.contributor.cotutor | Spinella, Aldo | en_US |
| dc.contributor.cotutor | Bella, Marco | en_US |
| dc.identifier.Dipartimento | Chimica e Biologia | en_US |
