Enantioselective [2+2]-Cycloaddition reactions of unsymmetrical cyclic ketenes with imines: synthesis of modified prolines and theoretical study of the reaction mechanism (Articolo in rivista)

Type

• Articolo in rivista (Classe)
• Prodotto della ricerca (Classe)

Label

• Enantioselective [2+2]-Cycloaddition reactions of unsymmetrical cyclic ketenes with imines: synthesis of modified prolines and theoretical study of the reaction mechanism (Articolo in rivista) (literal)

Anno

• 2004-01-01T00:00:00+01:00 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi

• 10.1021/jo040163w (literal)

Alternative label

• A. Macìas, E. Alonso, C. Del Pozo, A. Venturini and J. Gonzalez (2004)
  Enantioselective [2+2]-Cycloaddition reactions of unsymmetrical cyclic ketenes with imines: synthesis of modified prolines and theoretical study of the reaction mechanism
  in Journal of organic chemistry
  (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

• A. Macìas, E. Alonso, C. Del Pozo, A. Venturini and J. Gonzalez (literal)

Pagina inizio

• 7004 (literal)

Pagina fine

• 7012 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

• 69 (literal)

Rivista

• Journal of organic chemistry (Rivista)

Note

• ISI Web of Science (WOS) (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

• CNR (literal)

Titolo

• Enantioselective [2+2]-Cycloaddition reactions of unsymmetrical cyclic ketenes with imines: synthesis of modified prolines and theoretical study of the reaction mechanism (literal)

Abstract

• The synthesis of enantiomerically pure modified proline derivatives was achieved by using spiro ?-lactams as starting material that were prepared in turn by the [2+2]-cycloaddition of unsymmetrical cyclic ketenes with optically active imines. A theoretical study of the [2+2]-cycloaddition reaction, using density-functional methods, gave insights on the origin of the observed stereoselectivity of the Staudinger reaction. The spiro ?-lactams were transformed in the N-Boc derivatives and subjected to nucleophilic ring opening, affording the corresponding enantiomerically pure modified proline derivatives, isolated as orthogonally protected compounds. (literal)

Prodotto di

• MAteriali Funzionali Organici per applicazioni High-Tech: sistemi molecolari, supramolecolari e bioibridi (MAFO-HT) (PM.P04.003.003) (Modulo)
• Institute for organic syntheses and photoreactivity (ISOF) (Istituto)

Autore CNR

• ALESSANDRO VENTURINI (Unità di personale interno)

Incoming links:

Prodotto

• Institute for organic syntheses and photoreactivity (ISOF) (Istituto)
• MAteriali Funzionali Organici per applicazioni High-Tech: sistemi molecolari, supramolecolari e bioibridi (MAFO-HT) (PM.P04.003.003) (Modulo)

Autore CNR di

• ALESSANDRO VENTURINI (Unità di personale interno)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi

• Journal of organic chemistry (Rivista)