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Diastereoselective reductive nitro-Mannich reactions.

Anderson, JC; Blake, AJ; Koovits, PJ; Stepney, GJ; (2012) Diastereoselective reductive nitro-Mannich reactions. J Org Chem , 77 (10) 4711 - 4724. 10.1021/jo300535h.

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A range of nitroalkenes 1 and imines 3 derived from alkyl, aryl, and heteroaryl aldehydes underwent a tandem 1,4-hydride addition nitro-Mannich reaction to afford anti-rich β-nitroamines 4. The crude anti-β-nitroamines 4 could be converted to the corresponding anti-β-nitroacetamides 5 (33 examples) to allow purification in good yield from the parent nitroalkenes (60-87%), and with a high diastereomeric ratio (90:10 to mostly >95:5). A representative selection of anti-β-nitroacetamides 5 (five examples) were reduced to vicinal diamines 7 with zinc hydrochloride; concomitant acyl migration provided differentially protected vicinal diamines 7 in good yield (80-91%).

Title:Diastereoselective reductive nitro-Mannich reactions.
Location:United States
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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