title: Diastereoselective reductive nitro-Mannich reactions.
abstract: 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%).
authors.affiliation: Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, UK. j.c.anderson@ucl.ac.uk
authors.forename: James C
authors.initials: JC
authors.lastname: Anderson
authors.forename: Alexander J
authors.initials: AJ
authors.lastname: Blake
authors.forename: Paul J
authors.initials: PJ
authors.lastname: Koovits
authors.forename: Gregory J
authors.initials: GJ
authors.lastname: Stepney