Carella, Andrea
(2012)
Trasformazioni asimmetriche indotte da cristallizzazione di miscele diastereoisomeriche di aldeidi alpha-epimerizzabili.
[Laurea magistrale], Università di Bologna, Corso di Studio in
Chimica industriale [LM-DM270]
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Abstract
In the last few years organic chemistry has focused attention on enantiomeric resolution.
Among the several techiniques, crystallization-induced diastereoisomeric transformation
(CIDT) aroused the interest because of high yields, as well as to meet the criteria of
green chemistry. The process is applied in the specific way for a racemic mixtures of α-
epimerizable aldehydes, in order to obtain enatiomerically enrichment mixtures. This
technique involves the transformation of a racemic mixture of enantiomers into a
diasteroisomeric one by a reaction with a enantiopure auxiliary (Betti’s base). Then, to
mixture of diastereoisomers is applied the acid-catalyzed enrichment process: in solution,
the epimerization of more soluble diastereoisomer occurs, accompanied by precipitation
and hence the removal of the less soluble one from the equilibrium. Finally, through the
hydrolysis reaction, it was possible to recover the enantiomerically enriched aldehydes.
Abstract
In the last few years organic chemistry has focused attention on enantiomeric resolution.
Among the several techiniques, crystallization-induced diastereoisomeric transformation
(CIDT) aroused the interest because of high yields, as well as to meet the criteria of
green chemistry. The process is applied in the specific way for a racemic mixtures of α-
epimerizable aldehydes, in order to obtain enatiomerically enrichment mixtures. This
technique involves the transformation of a racemic mixture of enantiomers into a
diasteroisomeric one by a reaction with a enantiopure auxiliary (Betti’s base). Then, to
mixture of diastereoisomers is applied the acid-catalyzed enrichment process: in solution,
the epimerization of more soluble diastereoisomer occurs, accompanied by precipitation
and hence the removal of the less soluble one from the equilibrium. Finally, through the
hydrolysis reaction, it was possible to recover the enantiomerically enriched aldehydes.
Tipologia del documento
Tesi di laurea
(Laurea magistrale)
Autore della tesi
Carella, Andrea
Relatore della tesi
Correlatore della tesi
Scuola
Corso di studio
Ordinamento Cds
DM270
Parole chiave
enantiomeric resolution, crystallization-induced diastereoisomeric transformation (S)-Betti's Base, Aldheydes alpha-substituted
Data di discussione della Tesi
19 Ottobre 2012
URI
Altri metadati
Tipologia del documento
Tesi di laurea
(?? magistrale ??)
Autore della tesi
Carella, Andrea
Relatore della tesi
Correlatore della tesi
Scuola
Corso di studio
Ordinamento Cds
DM270
Parole chiave
enantiomeric resolution, crystallization-induced diastereoisomeric transformation (S)-Betti's Base, Aldheydes alpha-substituted
Data di discussione della Tesi
19 Ottobre 2012
URI
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