1448990-99-5Relevant academic research and scientific papers
Synthesis of diastereomeric pyrrolidine sulfamides via anchimerically assisted nucleophilic substitution reactions
Vargas-Caporali, Jorge,van der Lee, Arie,Dewynter, Georges,Juaristi, Eusebio
, p. 352 - 358 (2018/05/22)
The Mitsunobu reaction was employed in a key step during the development of a convenient synthetic route for the enantioselective preparation of pyrrolidine-sulfamide ligands from (R)- or (S)- [(S)-1-benzylpyrrolidin-2-yl](phenyl)methanol, and employing tert-butyl pyrrolidin-1-yl-sulfonylcarbamate as a non-conventional nucleophilic source. Although it is well documented that the exposure of this type of diastereomeric amino alcohols to the above-mentioned nucleophile usually leads to the formation of piperidines via ring expansion, either through classical nucleophilic substitution or the Mitsunobu version, only the pyrrolidine derivatives were generated with retention of configuration on the exocyclic stereocenter, owing to the neighboring group participation (internal backside nucleophilic substitution, SNib). Final removal of the N-Boc protecting group from the sulfamide fragment afforded chiral compounds with significant potential as chiral ligands in asymmetric catalysis.
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 (2013/08/23)
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.
