Lipase-catalysed kinetic resolution as the key step in the synthesis of a new class of optically active 5,6-trans-9,10-dihydrophenanthroline derivatives (Articolo in rivista)

Type
Label
  • Lipase-catalysed kinetic resolution as the key step in the synthesis of a new class of optically active 5,6-trans-9,10-dihydrophenanthroline derivatives (Articolo in rivista) (literal)
Anno
  • 2008-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/j.tetasy.2008.09.010 (literal)
Alternative label
  • Sanfilippo Claudia; Nicolosi Giovanni (2008)
    Lipase-catalysed kinetic resolution as the key step in the synthesis of a new class of optically active 5,6-trans-9,10-dihydrophenanthroline derivatives
    in Tetrahedron: asymmetry (Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Sanfilippo Claudia; Nicolosi Giovanni (literal)
Pagina inizio
  • 2171 (literal)
Pagina fine
  • 2176 (literal)
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  • 19 (literal)
Rivista
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  • 6 (literal)
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  • 18 (literal)
Note
  • Scopu (literal)
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Istituto di Chimica Biomolecolare del CNR, Via del Santuario 110, I-95028 Valverde CT, Italy (literal)
Titolo
  • Lipase-catalysed kinetic resolution as the key step in the synthesis of a new class of optically active 5,6-trans-9,10-dihydrophenanthroline derivatives (literal)
Abstract
  • New atropisomeric 5,6-trans-9,10-dihydrophenanthroline amino- and hydroxy-derivatives 3-7 possessing two additional stereogenic centres were obtained in high enantiomeric purity by lipase-catalysed kinetic resolution of the corresponding easily accessible racemates. Lipase from Pseudomonas fluorescens (Lipase AK) showed good enantioselectivity (E > 200) in the esterification reaction of trans-5-azido-6-hydroxyl derivative (±)-7, giving access to the enantioforms (+)- and (-)-7 isolated with ee = 97% and ee >98%, respectively. The chemical reduction of azide group furnished the homochiral amino derivatives (+)- and (-)-4 without a loss in enantiomeric purity. For all the substrates investigated, lipase AK revealed a stereopreference for the enantiomer with a (P,R,R)-configuration. (literal)
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