537703-93-8Relevant academic research and scientific papers
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
supporting information, p. 2752 - 2762 (2013/10/22)
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.
Synthesis of enantiopure amino polyols and pyrrolidine derivatives from 5-bromo-1,2-oxazin-4-ones
Pulz, Robert,Schade, Wolfgang,Reissig, Hans-Ulrich
, p. 405 - 407 (2007/10/03)
Diastereoselective electrophilic bromination of 3,6-dihydro-2H-1,2-oxazines syn-1 and anti-1 led to 5-bromo-1,2-oxazin-4-ones 2a and 3a, respectively. Reduction furnished 1,2-oxazin-4-ones 4 and 6 which could be transformed into enantiopure amino and imin
