1448991-03-4Relevant articles and documents
New class of bifunctional thioureas from l-proline: Highly enantioselective Michael addition of 1,3-dicarbonyls to nitroolefins
Vinayagam, Poopathy,Vishwanath, Manjunatha,Kesavan, Venkitasamy
, p. 568 - 577 (2014/05/06)
A new class of bifunctional tertiary amine thiourea was synthesized from l-proline. The reported thiourea is amenable to steric and electronic modifications at the stereogenic center bearing a thiourea moiety. Excellent enantioselectivity was obtained in the Michael addition of 2,4-pentanedione to various nitro olefins using the new organocatalyst. The construction of contiguous stereocenters via the Michael reaction of substituted 1,3-dicarbonyls to nitro olefins was also carried out with very good yield, enantioselectivity, and diastereoselectivity.
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.
