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41.1.1.5.13 Method 13: Aza-Henry Reaction

DOI: 10.1055/sos-SD-041-00002

Aitken, R. A.; Aitken, K. M.Science of Synthesis, (201041137.

In the aza-Henry reaction, a nitroalkane reacts with an imine to give a 2-nitroamine. Good stereoselectivity can be achieved using phase-transfer catalysis, in which cinchonidine derivative 315 has been found to be very efficient. The reaction shown in Scheme 185 was published independently by two separate groups.[‌548‌,‌549‌]

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888 (eee%) Meee Meeeeeeeee ee (%) Meeee (%) Mee
88 MMM MeMM8 (8 eeeee), 88°M 88 88 [‌888‌]
88 MeMMM8M MeMM8 (8 eeeee), 88°M 88 88 [‌888‌]

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References