期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 22, 期 28, 页码 9528-9532出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201601501
关键词
asymmetric catalysis; homogeneous catalysis; hydrogenation; pyridines; reaction mechanisms
资金
- European Commission [ITN-EID REDUCTO] [PITN-GA-2012-316371]
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 values up to 90%. The role of the base was elucidated with 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.
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