Chemo-enzymatic synthesis of new chiral bipyridyl alcohols and their atropisomeric N,N-dioxides (Articolo in rivista)

Type

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

Label

• Chemo-enzymatic synthesis of new chiral bipyridyl alcohols and their atropisomeric N,N-dioxides (Articolo in rivista) (literal)

Anno

• 2012-01-01T00:00:00+01:00 (literal)

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

• 10.2174/138527212800840946 (literal)

Alternative label

• Sanfilippo Claudia; Nicolosi Giovanni; Patti Angela (2012)
  Chemo-enzymatic synthesis of new chiral bipyridyl alcohols and their atropisomeric N,N-dioxides
  in Current organic chemistry; Bentham science publishers, Sharjah (Emirati Arabi Uniti)
  (literal)

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

• Sanfilippo Claudia; Nicolosi Giovanni; Patti Angela (literal)

Pagina inizio

• 1636 (literal)

Pagina fine

• 1644 (literal)

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

• http://www.benthamdirect.org/pages/b_viewarticle.php?articleID=3178144 (literal)

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

• 16 (literal)

Rivista

• Current organic chemistry (Rivista)

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

• 9 (literal)

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

• 13 (literal)

Note

• ISI Web of Science (WOS) (literal)

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

• CNR - Istituto di Chimica Biomolecolare, Via Paolo Gaifami 18, I-95127 Catania, Italy (literal)

Titolo

• Chemo-enzymatic synthesis of new chiral bipyridyl alcohols and their atropisomeric N,N-dioxides (literal)

Abstract

• New chiral bipyridyl alcohols and the corresponding N,N-dioxide derivatives were obtained with high enantiomeric excess by a chemo-enzymatic procedure. Metalation of commercial 6,6'-dimethyl-2,2'-bipyridine followed by reaction with acetaldehyde furnished an inseparable 1:1 mixture of dl- and meso- 6,6'-bis(2-hydroxypropyl)-2,2'-bipyridine ((±)-7a and meso-7b) that was subjected to lipasecatalysed enantioselective esterification with vinyl acetate in organic solvent. Immobilised Mucor Miehei lipase (Lipozyme ® IM) displayed high stereoselectivity and unreacted alcohol (S,S)-7a, monoacetyl derivative (R,S)-6 and diacetate (R,R)-9 were obtained in high optical purities as the result of the simultaneous resolution of the racemate and desymmetrization of meso isomer. After separation, the chiral compounds were converted into the corresponding N,N-dioxide derivatives with additional axial chirality stereoselectively induced during the N,N-oxidation and some considerations about their stereochemistry and atropisomeric stability were deduced by circular dichroism spectroscopy. (literal)

Editore

• Bentham science publishers (Editore)

Prodotto di

• Sintesi di sintoni chirali e molecole multifunzionalizzate per impiego biomedico (PM.P01.025.005) (Modulo)
• Istituto di chimica biomolecolare (ICB) (Istituto)

Autore CNR

• CLAUDIA SANFILIPPO (Persona)
• GIOVANNI NICOLOSI (Unità di personale interno)
• ANGELA PATTI (Persona)

Insieme di parole chiave

• Keywords of "Chemo-enzymatic synthesis of new chiral bipyridyl alcohols and their atropisomeric N,N-dioxides" (Insieme di parole chiave)

Incoming links:

Autore CNR di

• CLAUDIA SANFILIPPO (Persona)
• ANGELA PATTI (Persona)
• GIOVANNI NICOLOSI (Unità di personale interno)

Prodotto

• Istituto di chimica biomolecolare (ICB) (Istituto)
• Sintesi di sintoni chirali e molecole multifunzionalizzate per impiego biomedico (PM.P01.025.005) (Modulo)

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

• Current organic chemistry (Rivista)

Editore di

• Bentham science publishers (Editore)

Insieme di parole chiave di

• Keywords of "Chemo-enzymatic synthesis of new chiral bipyridyl alcohols and their atropisomeric N,N-dioxides" (Insieme di parole chiave)