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Iodination of carbohydrate-derived 1,2-oxazines to enantiopure 5-iodo-3,6-dihydro-2H-1,2-oxazines and subsequent palladium-catalyzed cross-coupling reactions
Medvecky, Michal ;  Linder, Igor ;  Schefzig, Luise ;  Reissig, Hans-Ulrich ;  Zimmer, Reinhold

HaupttitelIodination of carbohydrate-derived 1,2-oxazines to enantiopure 5-iodo-3,6-dihydro-2H-1,2-oxazines and subsequent palladium-catalyzed cross-coupling reactions
AutorMedvecky, Michal
AutorLinder, Igor
AutorSchefzig, Luise
AutorReissig, Hans-Ulrich
AutorZimmer, Reinhold
Seitenzahl8 S.
Freie Schlagwörteramino alcohol; click reaction; cross-coupling reactions; hydrogenation; iodination; 1,2-oxazines
DDC540 Chemie
Auch erschienen inBeilstein J. Org. Chem. - 12 (2016), S. 2898-2905
ZusammenfassungIodination of carbohydrate-derived 3,6-dihydro-2H-1,2-oxazines of type 3 using iodine and pyridine in DMF furnished 5-iodo-substituted 1,2-oxazine derivatives 4 with high efficacy. The alkenyl iodide moiety of 1,2-oxazine derivatives syn-4 and anti-4 was subsequently exploited for the introduction of new functionalities at the C-5 position by applying palladium-catalyzed carbon–carbon bond-forming reactions such as Sonogashira, Heck, or Suzuki coupling reactions as well as a cyanation reaction. These cross-coupling reactions led to a series of 5-alkynyl-, 5-alkenyl-, 5-aryl- and 5-cyano-substituted 1,2-oxazine derivatives being of considerable interest for further synthetic elaborations. This was exemplarily demonstrated by the hydrogenation of syn-21 and anti-24 and by a click reaction of a 5-alkynyl-substituted precursor.
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Fachbereich/EinrichtungFB Biologie, Chemie, Pharmazie
Erscheinungsjahr2016
Dokumententyp/-SammlungenWissenschaftlicher Artikel
SpracheEnglisch
RechteCreative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.
Anmerkungen des AutorsDer Artikel wurde in einer reinen Open-Access-Zeitschrift publiziert.
Erstellt am17.02.2017 - 11:47:34
Letzte Änderung17.02.2017 - 11:54:57
 
Statische URLhttp://edocs.fu-berlin.de/docs/receive/FUDOCS_document_000000026365
DOI10.3762/bjoc.12.289
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