期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 358, 期 16, 页码 2589-2593出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201600348
关键词
asymmetric catalysis; homogeneous catalysis; hydrogenation; pyridines; reaction mechanisms
资金
- European Commission [ITN-EID REDUCTO] [PITN-GA-2012-316371]
Herein we describe a new methodology for the asymmetric hydrogenation (AH) of 2-substituted pyridinium salts. An iridium catalyst based on a mixture of a chiral monodentate phosphoramidite and an achiral phosphine was shown to hydrogenate N-benzyl-2-arylpyiridinium bromides to the corresponding N-benzyl-2-arylpiperidines with full conversion and good enantioselectivity. The mechanism of the reaction under optimized conditions was investigated via kinetic measurements and isotopic labeling experiments. Our study suggests that the hydrogenation starts with a 1,4-hydride addition and that the enantiodiscriminating step involves the reduction of an iminium intermediate.
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