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.