Double nitro-Mannich reaction utilizing in situ generated N-trimethylsilylaldimines: novel four-component one-pot synthesis of nitroimines

Four-component synthesis of nitroimine derivatives (3) via double nitro-Mannich reaction was carried out in which nitroalkane, two moles of aldehyde, and lithium hexamethyldisilazide (LHMDS) were coupled in one-pot. In situ generated N-trimethylsilylaldimine was reacted with nitroalkane dianion followed by the second addition of the resulting nitrogen anion to the aldimine and the subsequent elimination of bistrimethylsilylamine furnished nitoroimine. The reaction was proceeded with erythro selectivity.