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.

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