Abstract:
Reactions of (E)-1,1,1-trichloro(trifluoro)-3-nitrobut-2-enes with 3,3-dimethyl-2-morpholinobutene in benzene give (4R*,6R*)-6-tert-butyl-3-methyl-6-morpholino-4-trihalomethyl-5,6-dihydro-4H-1,2-oxazine 2-oxides. In a dichloromethane solution, these cyclic nitronates undergo diastereoselective ring opening to produce nitroalkylated anti-CCl3- and syn-CF3-enamines, which are hydrolysed with dilute HCl to afford the respective anti-CCl3- and syn-CF3-g-nitroketones.
Citation:
V. Yu. Korotaev, A. Yu. Barkov, P. A. Slepukhin, M. I. Kodess, V. Ya. Sosnovskikh, “Diastereoselective reactions of 1,1,1-trichloro(trifluoro)-3-nitrobut-2-enes with 2-morpholinoalk-1-enes”, Mendeleev Commun., 21:2 (2011), 112–114
Linking options:
https://www.mathnet.ru/eng/mendc2885
https://www.mathnet.ru/eng/mendc/v21/i2/p112
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