<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