title: Anti-Selective Organocatalytic Michael Addition between Phenylacetaldehyde and Nitrostyrene.
abstract: 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 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.
authors.affiliation: Laboratory of Organic Synthesis, Center of Research and Development in Chemistry, National Institute of Industrial Technology , Buenos Aires, Argentina.
authors.forename: Lucía Gandolfi
authors.initials: LG
authors.lastname: Donadío
authors.affiliation: Laboratory of Organic Synthesis, Center of Research and Development in Chemistry, National Institute of Industrial Technology , Buenos Aires, Argentina.
authors.forename: Mariana A
authors.initials: MA
authors.lastname: Galetti
authors.affiliation: Department of Biotechnologies, Chemistry & Pharmacy, University of Siena , 53100 Siena, Italy.
authors.forename: Gianluca
authors.initials: G
authors.lastname: Giorgi
authors.affiliation: Chemessentia SRL , 28100 Novara, Italy.
authors.forename: Marcello
authors.initials: M
authors.lastname: Rasparini
authors.affiliation: Laboratory of Organic Synthesis, Center of Research and Development in Chemistry, National Institute of Industrial Technology , Buenos Aires, Argentina.
authors.forename: Maria J
authors.initials: MJ
authors.lastname: Comin