Synthesis of chiral beta(2,2,3)-3-amino-2-hydroxyalkanoates and 3-alkyl-3-hydroxy-beta-lactams by double asymmetric induction (Articolo in rivista)

Type

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

Label

• Synthesis of chiral beta(2,2,3)-3-amino-2-hydroxyalkanoates and 3-alkyl-3-hydroxy-beta-lactams by double asymmetric induction (Articolo in rivista) (literal)

Anno

• 2007-01-01T00:00:00+01:00 (literal)

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

• 10.1016/j.tet.2007.05.069 (literal)

Alternative label

• Guerrini A.; Varchi G.; Rizzo D.; Samori C.; Battaglia A. (2007)
  Synthesis of chiral beta(2,2,3)-3-amino-2-hydroxyalkanoates and 3-alkyl-3-hydroxy-beta-lactams by double asymmetric induction
  in Tetrahedron (Oxf., Print)
  (literal)

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

• Guerrini A.; Varchi G.; Rizzo D.; Samori C.; Battaglia A. (literal)

Pagina inizio

• 7949 (literal)

Pagina fine

• 7969 (literal)

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

• 63 (literal)

Rivista

• Tetrahedron (Rivista)

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

• 33 (literal)

Note

• ISI Web of Science (WOS) (literal)

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

• Ist CNR Sintesi Organ Fotoreattivita ISOF, Area Ric Bologna, I-40129 Bologna, Italy (literal)

Titolo

• Synthesis of chiral beta(2,2,3)-3-amino-2-hydroxyalkanoates and 3-alkyl-3-hydroxy-beta-lactams by double asymmetric induction (literal)

Abstract

• Reactions of chiral (2S)-enolates of dioxolan-4-ones, derived from lactic, mandelic, and phenyllactic acids, with aliphatic (S-S)and (S-R)-tert-butylsulfinyl aldimines afforded conformationally restrained C2-disubstituted N,O-orthogonally protected 3-amino-2-hydroxyalkanoates in the form of N-sulfinyl protected 1'-aminodioxolan-4-ones. The product distribution showed that there is significant kinetic selectivity, due to the presence of 'matched' and 'mismatched' components, between the (S)-or (R)-tert-butylsulfinyl aldimines and the (2S)enolates of the 1,3-dioxolan-4-ones. Selective methoxide- induced removal of the acetal group of the N-sulfinyl-1'-aminodioxolanones yielded the corresponding N-sulfinyl protected methyl alkanoates. In addition, the selective acid-induced removal of the sulfinyl group of the N-sulfinyl-1'- aminodioxolanones provided the corresponding N-unprotected 1'-aminodioxolanones, whose base-induced cyclization afforded the corresponding beta-lactams. (literal)

Prodotto di

• Institute for organic syntheses and photoreactivity (ISOF) (Istituto)
• Sintesi e caratterizzazione mediante metodologie chimiche innovative, di scaffold molecolari per l'individuazione di nuove molecole biologicamente attive. (PM.P03.011.002) (Modulo)

Autore CNR

• ARTURO BATTAGLIA (Unità di personale interno)
• GRETA VARCHI (Unità di personale interno)
• ANDREA GUERRINI (Persona)

Incoming links:

Prodotto

• Institute for organic syntheses and photoreactivity (ISOF) (Istituto)
• Sintesi e caratterizzazione mediante metodologie chimiche innovative, di scaffold molecolari per l'individuazione di nuove molecole biologicamente attive. (PM.P03.011.002) (Modulo)

Autore CNR di

• ARTURO BATTAGLIA (Unità di personale interno)
• GRETA VARCHI (Unità di personale interno)
• ANDREA GUERRINI (Persona)

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

• Tetrahedron (Rivista)