RT info:eu-repo/semantics/article
T1 Enantiodivergent Synthesis of (+)- and (-)-Pyrrolidine 197B. Synthesis of trans-2,5-Disubstituted Pyrrolidines via Intramolecular Hydroamination
A1 Pérez, Sixto J.
A1 Purino, Martín A.
A1 Cruz, Daniel A.
A1 López-Soria, Juan M.
A1 Carballo, Rubén M.
A1 Ramírez, Miguel A.
A1 Fernández, Israel
A1 Martín García, Víctor Sotero
A1 Padrón, Juan I.
K1 Alcaloides
K1 ciclización
K1 hidroaminación
K1 acero
K1 heterociclos de nitrógeno
AB A highly efficient diastereoselective iron(III)-catalyzed intramolecular hydroamination/cyclization reaction involving - substituted amino alkenes is described. Thus, enantiopure trans-2,5- disubstituted pyrrolidines and trans-5-substituted proline derivatives are synthesized by means of the combination of enantiopure starting materials, easily available from L--amino acids, with sustainable metal catalysts such as iron(III) salts. The scope of this methodology is highlighted in an enantiodivergent approach to the synthesis of both (+)- and (-)-pyrrolidine 197B alkaloids from L-glutamic acid. In addition, a computational study was also carried out to gain insight into the complete diastereoselectivity of the transformation.
PB Wiley
YR 2016
FD 2016
LK http://riull.ull.es/xmlui/handle/915/16011
UL http://riull.ull.es/xmlui/handle/915/16011
LA en
DS Repositorio institucional de la Universidad de La Laguna
RD 26-dic-2024