jo6b01061_si_002.pdf (2.59 MB)
Anti-Selective Organocatalytic Michael Addition between Phenylacetaldehyde and Nitrostyrene
journal contribution
posted on 2016-07-21, 00:00 authored by Lucía
Gandolfi Donadío, Mariana A. Galetti, Gianluca Giorgi, Marcello Rasparini, Maria J. CominUsing 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 anti adduct was obtained in high yield and diastereoselection as was
demonstrated by the X-ray structure of the product. In situ NMR studies showed a different reaction pathway when compared to
aliphatic aldehydes that yield the syn adduct as
major isomer.