1448991-01-2Relevant academic research and scientific papers
Synthesis of versatile bifunctional derivatives of chiral diamines obtained through anchimerically assisted nucleophilic substitution reactions on diastereomeric phenylprolinols
Vargas-Caporali, Jorge,Cruz-Hernandez, Carlos,Juaristi, Eusebio
, p. 1275 - 1300 (2012)
Diastereomeric [(S)-1-benzylpyrrolidin-2-yl]-(R)-[(phenyl)- methanamine] and [(S)-1-benzylpyrrolidin-2-yl]-(S)-[(phenyl)methanamine], were synthesized by selective internal backside nucleophilic substitution of the corresponding activated phenylprolinols. X-Ray diffraction structures of crystalline acetamide derivatives confirmed the anticipated stereochemistry for a SNib reaction mechanism. In order to apply this reaction to the synthesis of bifunctional analogs, a series of fragments such as a thiourea moiety and sulfonamide functions were introduced for the functionalization of the primary amino group in the substrate, obtaining more stable and potentially useful derivatives.
