10.1021/acs.joc.6b01061.s002 Lucía Gandolfi Donadío Lucía Gandolfi Donadío Mariana A. Galetti Mariana A. Galetti Gianluca Giorgi Gianluca Giorgi Marcello Rasparini Marcello Rasparini Maria J. Comin Maria J. Comin <i>Anti</i>-Selective Organocatalytic Michael Addition between Phenylacetaldehyde and Nitrostyrene American Chemical Society 2016 organocatalytic Michael reactions syn adduct NMR studies aliphatic aldehydes diastereochemical outcome benzylic aldehydes Selective Organocatalytic Michael Addition nitrostyrene reaction pathway 2016-07-21 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/_i_Anti_i_-Selective_Organocatalytic_Michael_Addition_between_Phenylacetaldehyde_and_Nitrostyrene/3506648 Using the reaction between phenylacetaldehyde and nitrostyrene catalyzed by pyrrolidine as a simple model, we have studied the diastereochemical outcome of the organocatalytic Michael reactions between benzylic aldehydes and nitrostyrenes. We found that the <i>anti</i> adduct was obtained in high yield and diastereoselection as was demonstrated by the X-ray structure of the product. <i>In situ</i> NMR studies showed a different reaction pathway when compared to aliphatic aldehydes that yield the <i>syn</i> adduct as major isomer.