A Straightforward Synthesis of Enantiopure 2,6-Disubstituted Morpholines by Regioselective O-Protection/Activation Protocol (Articolo in rivista)

Type
Label
  • A Straightforward Synthesis of Enantiopure 2,6-Disubstituted Morpholines by Regioselective O-Protection/Activation Protocol (Articolo in rivista) (literal)
Anno
  • 2008-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1055/s-2008-1078054 (literal)
Alternative label
  • Penso, M.; Lupi, V.; Albanese, D.; Foschi, F.; Landini, D.; Tagliabue, A. (2008)
    A Straightforward Synthesis of Enantiopure 2,6-Disubstituted Morpholines by Regioselective O-Protection/Activation Protocol
    in Synlett (Stuttg.)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Penso, M.; Lupi, V.; Albanese, D.; Foschi, F.; Landini, D.; Tagliabue, A. (literal)
Pagina inizio
  • 2451 (literal)
Pagina fine
  • 2454 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • https://www.thieme-connect.de/DOI/DOI?10.1055/s-2008-1078054 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 16 (literal)
Rivista
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • CNR-ISTM, Milano. Dipartimento di Chimica Organica e Industriale dellÂ’Università degli Studi di Milano. Nerviano Medical Sciences. (literal)
Titolo
  • A Straightforward Synthesis of Enantiopure 2,6-Disubstituted Morpholines by Regioselective O-Protection/Activation Protocol (literal)
Abstract
  • Enantiopure 2,6-disubstituted morpholines have been synthesized through the ring opening of chiral, nonracemic oxiranes with nitrogen nucleophiles, under solid-liquid phase-transfer catalysis (SL-PTC) conditions. The beta-hydroxytosyl amides resulting from the ring opening of a first epoxide with TsNH2 was used as nucleophile, after protection of the hydroxyl group, in the reaction with a second oxirane. The morpholine skeleton has been generated through standard functional group chemistry, followed by cyclization of the intermediate beta-hydroxy-beta'-tosyloxy-tosylamides carried out under SL-PTC conditions. N-Tosyl morpholines produced can be employed as building blocks in the synthesis of pharmaceuticals and as chiral tools (literal)
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