Data di Pubblicazione:
2016
Citazione:
Asymmetric hydrogenation of 3-substituted pyridinium salts / M. Renom-Carrasco, P. Gajewski, L.L. Pignataro, J. De Vries, U. Piarulli, C. Gennari, L. Lefort. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 22:28(2016 Jul 04), pp. 9528-9532. [10.1002/chem.201601501]
Abstract:
The use of an equivalent amount of an organic base leads to high enantiomeric excess in the asymmetric hydrogenation of N-benzylated 3-substituted pyridinium salts into the corresponding piperidines. Indeed, in the presence of Et3N, a Rh-JosiPhos catalyst reduced a range of pyridinium salts with ee's up to 90%. The role of the base was elucidated via a mechanistic study involving the isolation of the various reaction intermediates and isotopic labeling experiments. Additionally, this study provided some evidence for an enantiodetermining step involving a dihydropyridine intermediate.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
hydrogenation; asymmetric catalysis; pyridines; homogeneous catalysis; reaction mechanisms
Elenco autori:
M. Renom-Carrasco, P. Gajewski, L.L. Pignataro, J. De Vries, U. Piarulli, C. Gennari, L. Lefort
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