Enantioselective addition of aryl ketones and acetone to nitroalkenes organocatalyzed by carbamate-monoprotected cyclohexa-1,2-diamines

Enantiomerically pure carbamate-monoprotected trans-cyclohexane-1,2-diamines are used as chiral organocatalysts for the addition of aryl ketones and acetone to nitroalkenes to give enantioenriched β-substituted γ-nitroketones. The reaction was performed in the presence of 3,4-dimethoxybenzoic acid as an additive, in chloroform as the solvent at room temperature, achieving enantioselectivities up to 96%. Theoretical calculations are used to justify the observed sense of the stereoinduction.

We thank the financial support from the Spanish Ministerio de Economía y Competitividad (project CTQ2011-24151), FEDER, the COST Action CM0905 ‘Organocatalysis’, the FP7 Marie Curie Action of the European Commission via the ITN ECHONET Network (FP7-MCITN-2012-316379), and the universities of Alicante and the Basque Country.