New routes to enantioenriched substances through small organic molecules
Contribuinte(s) |
Righi, Paolo |
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Data(s) |
27/04/2009
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Resumo |
In this thesis we will disclose the results obtained from the diastereoisomeric salt formation (n salt, p salt and p1,n1 salt) between non-racemic trans-chrysanthemic acid (trans-ChA) and pure enantiomers of threo-2-dimethylamino-1-phenyl-1,3-propanediol (DMPP). The occurrence of p1,n1 salt formation can have profound effects on enantiomer separation of scalemic (non-racemic) mixtures. This phenomenon when accompanied by substrate self-association impedes the complete recovery of the major enantiomer through formation of an inescapable racemate cage. A synthetic sequence for the asymmetric synthesis of bicyclo[3.2.0]heptanones and bicyclo[3.2.0]hept-3-en-6-ones through a cycloaddition strategy is reported. The fundamental step is a [2+2]-cycloaddition of an enantiopure amide derived from the reaction between a set of acids and an oxazolidinone as the chiral auxiliary. The inter- and intramolecular cycloaddition of in situ-generated keteniminium salts gives bicycles with a good enantioselection. A key intermediate of Iloprost, a chemically stable and biologically active mimic of prostacyclin PGI2 is synthesized following a ‘green approach’. An example of simple optical resolution of this racemic intermediate involving the diastereoisomeric salt formation is described. |
Formato |
application/pdf |
Identificador |
http://amsdottorato.unibo.it/1458/1/Boschi_Francesca_tesi.pdf urn:nbn:it:unibo-1265 Boschi, Francesca (2009) New routes to enantioenriched substances through small organic molecules, [Dissertation thesis], Alma Mater Studiorum Università di Bologna. Dottorato di ricerca in Scienze chimiche <http://amsdottorato.unibo.it/view/dottorati/DOT298/>, 21 Ciclo. DOI 10.6092/unibo/amsdottorato/1458. |
Idioma(s) |
en |
Publicador |
Alma Mater Studiorum - Università di Bologna |
Relação |
http://amsdottorato.unibo.it/1458/ |
Direitos |
info:eu-repo/semantics/openAccess |
Palavras-Chave | #CHIM/06 Chimica organica |
Tipo |
Tesi di dottorato NonPeerReviewed |