Asymmetric Hydrogenation of 3-Substituted Pyridinium Salts
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...
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| Vydáno v: | Chemistry : a European journal Ročník 22; číslo 28; s. 9528 - 9532 |
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WEINHEIM
Blackwell Publishing Ltd
04.07.2016
Wiley Wiley Subscription Services, Inc |
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| ISSN: | 0947-6539, 1521-3765, 1521-3765 |
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| 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 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.
Ariadne′s thread: The asymmetric hydrogenation of 3‐substitued pyridines has been achieved with up to 90 % ee. The use of an equivalent amount of an organic base turned out to be crucial to avoid unwanted pathways leading to non‐enantioselective reduction. An in‐depth investigation of the mechanism revealed a labyrinth of hydrogenation pathways with many dead ends (see figure). |
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| AbstractList | 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. 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 Et3 N, 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. 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 Et sub(3)N, 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. Ariadne's thread: The asymmetric hydrogenation of 3-substitued pyridines has been achieved with up to 90% ee. The use of an equivalent amount of an organic base turned out to be crucial to avoid unwanted pathways leading to non-enantioselective reduction. An in-depth investigation of the mechanism revealed a labyrinth of hydrogenation pathways with many dead ends (see figure). 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. Ariadne′s thread: The asymmetric hydrogenation of 3‐substitued pyridines has been achieved with up to 90 % ee. The use of an equivalent amount of an organic base turned out to be crucial to avoid unwanted pathways leading to non‐enantioselective reduction. An in‐depth investigation of the mechanism revealed a labyrinth of hydrogenation pathways with many dead ends (see figure). 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 Et3 N, 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.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 Et3 N, 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. 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 Et 3 N, 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. |
| Author | Gajewski, Piotr Renom-Carrasco, Marc de Vries, Johannes G. Lefort, Laurent Pignataro, Luca Piarulli, Umberto Gennari, Cesare |
| Author_xml | – sequence: 1 givenname: Marc surname: Renom-Carrasco fullname: Renom-Carrasco, Marc organization: DSM Ahead R&D B.V.-Innovative Synthesis, P. O. Box 18, 6160 MD, Geleen, The Netherlands – sequence: 2 givenname: Piotr surname: Gajewski fullname: Gajewski, Piotr organization: DSM Ahead R&D B.V.-Innovative Synthesis, P. O. Box 18, 6160 MD, Geleen, The Netherlands – sequence: 3 givenname: Luca surname: Pignataro fullname: Pignataro, Luca organization: Dipartimento di Chimica, Università degli Studi di Milano, via C. Golgi 19, 20133, Milan, Italy – sequence: 4 givenname: Johannes G. surname: de Vries fullname: de Vries, Johannes G. organization: Leibniz-Institut für Katalyse e.V. an der, Universität Rostock, Albert-Einstein-Str. 29a, 18059, Rostock, Germany – sequence: 5 givenname: Umberto surname: Piarulli fullname: Piarulli, Umberto organization: Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell'Insubria, via Valleggio 11, 22100, Como, Italy – sequence: 6 givenname: Cesare surname: Gennari fullname: Gennari, Cesare organization: Dipartimento di Chimica, Università degli Studi di Milano, via C. Golgi 19, 20133, Milan, Italy – sequence: 7 givenname: Laurent surname: Lefort fullname: Lefort, Laurent email: laurent.lefort@dsm.com organization: DSM Ahead R&D B.V.-Innovative Synthesis, P. O. Box 18, 6160 MD, Geleen, The Netherlands |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/27140832$$D View this record in MEDLINE/PubMed |
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| Keywords | SCOPE MONODENTATE PHOSPHORAMIDITE LIGANDS reaction mechanisms QUINOLINES asymmetric catalysis DEHYDROAMINO ACID-DERIVATIVES hydrogenation MULTIPLE STEREOGENIC CENTERS IRIDIUM-CATALYZED HYDROGENATION HIGHLY ENANTIOSELECTIVE HYDROGENATION pyridines homogeneous catalysis REDUCTION PIPERIDINES ISOQUINOLINIUM SALTS |
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Chem. |
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| Snippet | 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... 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... |
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| SubjectTerms | asymmetric catalysis Asymmetry Chemistry Chemistry, Multidisciplinary Equivalence homogeneous catalysis Hydrogenation Isotopic labeling Labyrinth Pathways Physical Sciences Piperidine Pyridines reaction mechanisms Salts Science & Technology |
| Title | Asymmetric Hydrogenation of 3-Substituted Pyridinium Salts |
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