1122571-80-5Relevant articles and documents
Convenient syntheses of enantiopure 1,2-oxazin-4-yl nonaflates and phosphates and their palladium-catalyzed cross-couplings
Moinizadeh, Nima,Klemme, Robby,Kansy, Marcus,Zimmer, Reinhold,Reissig, Hans-Ulrich
, p. 2752 - 2762 (2013)
Efficient methods to prepare enantiopure 1,2-oxazin-4-yl nonaflates and phosphates were elaborated. The corresponding 1,2-oxazin-4-ones were transformed into their enolates and then quenched with nonafluorobutanesulfonyl fluoride or diphenyl chlorophosphate to provide the title compounds. Alternatively, the corresponding α-bromo ketones were subjected to Perkow reactions efficiently leading to the respective enol phosphates. A variety of palladium-catalyzed cross-couplings such as Kumada-Corriu, Sonogashira, Heck reactions or borylation reactions were studied, which delivered the expected new 4-substituted 1,2-oxazine derivatives generally in satisfactory yields. A few typical subsequent transformations were studied including a copper-catalyzed [3+2] cycloaddition with a galactose-derived azide. They demonstrate the synthetic potential of the newly prepared enantiopure 4-substituted 1,2-oxazines. Georg Thieme Verlag Stuttgart · New York.
