Baker’'s yeast-mediated reduction of ethyl 2-(4-chlorophenoxy)-3-oxoalkanoates intermediates for potential PPARalpha ligands (Articolo in rivista)

Type

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

Label

• Baker’'s yeast-mediated reduction of ethyl 2-(4-chlorophenoxy)-3-oxoalkanoates intermediates for potential PPARalpha ligands (Articolo in rivista) (literal)

Anno

• 2004-01-01T00:00:00+01:00 (literal)

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

• 10.1016/j.tetasy.2004.08.027 (literal)

Alternative label

• Perrone M.G. 1, Santandrea E. 1 , Scilimati A. 1, Tortorella V. 1 , Capitelli F. 2, Bertolasi V. 3 (2004)
  Baker’'s yeast-mediated reduction of ethyl 2-(4-chlorophenoxy)-3-oxoalkanoates intermediates for potential PPARalpha ligands
  in Tetrahedron: asymmetry (Print); Pergamon-Elsevier Science Ltd., Oxford (Regno Unito)
  (literal)

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

• Perrone M.G. 1, Santandrea E. 1 , Scilimati A. 1, Tortorella V. 1 , Capitelli F. 2, Bertolasi V. 3 (literal)

Pagina inizio

• 3501 (literal)

Pagina fine

• 3510 (literal)

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

• 15 (literal)

Rivista

• Tetrahedron: asymmetry (Rivista)

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

• 9 (literal)

Note

• ISI Web of Science (WOS) (literal)

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

• 1- Dip. Farmaco-Chimico, Univ. di Bari 2- CNR-IC, Sede di Bari 3- Dip. di Chimica e Centro di Strutturistica Diffrattometrica, Univ. di Ferrara (literal)

Titolo

• Baker’'s yeast-mediated reduction of ethyl 2-(4-chlorophenoxy)-3-oxoalkanoates intermediates for potential PPARalpha ligands (literal)

Abstract

• Several 2-(4-chlorophenoxy)-3-oxoesters were prepared in fair to good yields and then reduced in the presence of baker's yeast to the corresponding alcohols having de's up to 92% and ee's > 99%. The absolute configuration of nearly enantiomerically pure ethyl 2-(4-chlorophenoxy)-3-hydroxybutanoate was assigned by both comparison of the sign of the specific rotation and HPLC retention times of authentic samples prepared from threonines. Reduction of ethyl 2-(4-chlorophenoxy)-3-oxo-4-phenylbutanoate afforded only enantiomerically pure ethyl (2R,3S)-2-(4-chlorophenoxy)-3-hydroxy-4-phenylbutanoate (out of the four possible stereoisomers), whose absolute configuration was established by single crystal X-ray analysis. Furthermore, reduction of ethyl 2-methyl-2-(4-chlorophenoxy)-3-hydroxybutanoate with a quaternary stereogenic carbon (C-2) gave both of the two expected diastereoisomers with ee = 95% and 96%. Insight into the mechanism of baker's yeast-mediated reduction of prochiral ketoesters is also reported. (literal)

Editore

• Pergamon-Elsevier Science Ltd. (Editore)

Prodotto di

• Institute of Crystallography (IC) (Istituto)
• Sviluppo e Applicazioni di Metodi Cristallografici (PM.P06.002.001) (Modulo)

Autore CNR

• FRANCESCO CAPITELLI (Unità di personale interno)

Insieme di parole chiave

• Parole chiave di "Baker’'s yeast-mediated reduction of ethyl 2-(4-chlorophenoxy)-3-oxoalkanoates intermediates for potential PPARalpha ligands" (Insieme di parole chiave)

Incoming links:

Prodotto

• Institute of Crystallography (IC) (Istituto)
• Sviluppo e Applicazioni di Metodi Cristallografici (PM.P06.002.001) (Modulo)

Autore CNR di

• FRANCESCO CAPITELLI (Unità di personale interno)

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

• Tetrahedron: asymmetry (Rivista)

Editore di

• Pergamon-Elsevier Science Ltd. (Editore)

Insieme di parole chiave di

• Parole chiave di "Baker’'s yeast-mediated reduction of ethyl 2-(4-chlorophenoxy)-3-oxoalkanoates intermediates for potential PPARalpha ligands" (Insieme di parole chiave)