Lithium diisopropylamide, reaction with nitroalkanes

Method C High awft -selectivity is also observed in the fluoride-catalyzed reaction of silyl nitronates with aldehydes. Trialkyl silyl nitronates are prepared in good yield from primary nitroalkanes by consecutive treatment with lithium diisopropylamide and trialkylsilyl chloride at -78 °C in THF. 

Another related method uses the anion of nitroalkanes in a reaction with halo-esters. Nitromethane reacted with lithium diisopropylamide to form the nitro enolate and then with methyl 3-chloropentanoatc to give 4.110. Reduction of the nitro group with ammonium formate gave methyl 2-phenyl-3-aminopropanoate, 4.111. 

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