<i>Anti</i>-Selective Organocatalytic Michael Addition between Phenylacetaldehyde and Nitrostyrene Lucía Gandolfi Donadío Mariana A. Galetti Gianluca Giorgi Marcello Rasparini Maria J. Comin 10.1021/acs.joc.6b01061.s001 https://acs.figshare.com/articles/dataset/_i_Anti_i_-Selective_Organocatalytic_Michael_Addition_between_Phenylacetaldehyde_and_Nitrostyrene/3506645 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. 2016-07-21 00:00:00 organocatalytic Michael reactions syn adduct NMR studies aliphatic aldehydes diastereochemical outcome benzylic aldehydes Selective Organocatalytic Michael Addition nitrostyrene reaction pathway