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231226s2022 xx |||||o 00| ||eng c |
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|a 10.1021/acs.organomet.2c00180
|2 doi
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|a eng
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|a Pavlovic, Ljiljana
|e verfasserin
|4 aut
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| 245 |
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|a Cobalt-Catalyzed Asymmetric Hydrogenation of Enamides
|b Insights into Mechanisms and Solvent Effects
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|c 2022
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|a Text
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|a ƒaComputermedien
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|a ƒa Online-Ressource
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|a Date Revised 01.09.2024
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|a published: Print
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|a Citation Status PubMed-not-MEDLINE
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|a © 2022 The Authors. Published by American Chemical Society.
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|a The mechanistic details of the (PhBPE)Co-catalyzed asymmetric hydrogenation of enamides are investigated using computational and experimental approaches. Four mechanistic possibilities are compared: a direct Co(0)/Co(II) redox path, a metathesis pathway, a nonredox Co(II) mechanism featuring an aza-metallacycle, and a possible enamide-imine tautomerization pathway. The results indicate that the operative mechanism may depend on the type of enamide. Explicit solvent is found to be crucial for the stabilization of transition states and for a proper estimation of the enantiomeric excess. The combined results highlight the complexity of base-metal-catalyzed hydrogenations but do also provide guiding principles for a mechanistic understanding of these systems, where protic substrates can be expected to open up nonredox hydrogenation pathways
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|a Journal Article
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|a Mendelsohn, Lauren N
|e verfasserin
|4 aut
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|a Zhong, Hongyu
|e verfasserin
|4 aut
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| 700 |
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|a Chirik, Paul J
|e verfasserin
|4 aut
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| 700 |
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|a Hopmann, Kathrin H
|e verfasserin
|4 aut
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| 773 |
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|i Enthalten in
|t Organometallics
|d 1998
|g 41(2022), 14 vom: 25. Juli, Seite 1872-1882
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|x 0276-7333
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|g volume:41
|g year:2022
|g number:14
|g day:25
|g month:07
|g pages:1872-1882
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|u http://dx.doi.org/10.1021/acs.organomet.2c00180
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