Anti-Selective Organocatalytic Michael Addition between Phenylacetaldehyde and Nitrostyrene
Lucía Gandolfi Donadío1, Mariana A Galetti1, Gianluca Giorgi2
1Laboratory of Organic Synthesis, Center of Research and Development in Chemistry, National Institute of Industrial Technology , Buenos Aires, Argentina.
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.
Related Concept Videos
Conjugate Addition of Enolates: Michael Addition
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
Aldehydes and Ketones with Alcohols: Hemiacetal Formation
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Radical Anti-Markovnikov Addition to Alkenes: Overview


