Ramos Ferronatto, Gabriel
(2013)
Dynamic resolution of alpha-substituted dihydrocinnamic aldehydes. A new asymmetric synthesis of pharmaceutically important amine building blocks.
[Laurea magistrale], Università di Bologna, Corso di Studio in
Advanced spectroscopy in chemistry [LM-DM270]
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Abstract
Crystallization-induced diastereoisomer transformation (CIDT) was successfully employed in the enantioselective synthesis of 2-alkyl-3-aryl-propan-1-amines. These products are seen as potentially useful building blocks in the field of asymmetric organic chemistry, notably for pharmaceutically relevant compounds. The procedure was based on a recently reported protocol for deracemization of dihydrocinnamic aldehydes in which enantiomerically enriched 1-(amino(phenyl)methyl)naphthalen-2-ol (Betti base) is employed as a resolving agent. Additionally, fenpropimorph, a biologically active substance which contains the 2-alkyl-3-aryl-propan-1-amine moiety was synthetized, as an attempt to assess the usefulness of the enantiomerically enriched amines.
Abstract
Crystallization-induced diastereoisomer transformation (CIDT) was successfully employed in the enantioselective synthesis of 2-alkyl-3-aryl-propan-1-amines. These products are seen as potentially useful building blocks in the field of asymmetric organic chemistry, notably for pharmaceutically relevant compounds. The procedure was based on a recently reported protocol for deracemization of dihydrocinnamic aldehydes in which enantiomerically enriched 1-(amino(phenyl)methyl)naphthalen-2-ol (Betti base) is employed as a resolving agent. Additionally, fenpropimorph, a biologically active substance which contains the 2-alkyl-3-aryl-propan-1-amine moiety was synthetized, as an attempt to assess the usefulness of the enantiomerically enriched amines.
Tipologia del documento
Tesi di laurea
(Laurea magistrale)
Autore della tesi
Ramos Ferronatto, Gabriel
Relatore della tesi
Scuola
Corso di studio
Ordinamento Cds
DM270
Parole chiave
organic chemistry asymmetric synthesis crystallization induced diastereoisomer transformation Betti base chiral amines
Data di discussione della Tesi
14 Ottobre 2013
URI
Altri metadati
Tipologia del documento
Tesi di laurea
(?? magistrale ??)
Autore della tesi
Ramos Ferronatto, Gabriel
Relatore della tesi
Scuola
Corso di studio
Ordinamento Cds
DM270
Parole chiave
organic chemistry asymmetric synthesis crystallization induced diastereoisomer transformation Betti base chiral amines
Data di discussione della Tesi
14 Ottobre 2013
URI
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