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Renom-Carrasco M, Gajewski P, Pignataro L, et al. Asymmetric Hydrogenation of 3-Substituted Pyridinium Salts. Chemistry. 2016;22(28):9528-32doi: 10.1002/chem.201601501.
Renom-Carrasco, M., Gajewski, P., Pignataro, L., de Vries, J. G., Piarulli, U., Gennari, C., & Lefort, L. (2016). Asymmetric Hydrogenation of 3-Substituted Pyridinium Salts. Chemistry (Weinheim an der Bergstrasse, Germany), 22(28), 9528-32. https://doi.org/10.1002/chem.201601501
Renom-Carrasco, Marc, et al. "Asymmetric Hydrogenation of 3-Substituted Pyridinium Salts." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,28 (2016): 9528-32. doi: https://doi.org/10.1002/chem.201601501
Renom-Carrasco M, Gajewski P, Pignataro L, de Vries JG, Piarulli U, Gennari C, Lefort L. Asymmetric Hydrogenation of 3-Substituted Pyridinium Salts. Chemistry. 2016 Jul 04;22(28):9528-32. doi: 10.1002/chem.201601501. Epub 2016 Jun 03. PMID: 27140832.
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Chemistry. 2016 Jul 04;22(28):9528-32. doi: 10.1002/chem.201601501. Epub 2016 Jun 03.

Asymmetric Hydrogenation of 3-Substituted Pyridinium Salts.

Chemistry (Weinheim an der Bergstrasse, Germany)

Marc Renom-Carrasco, Piotr Gajewski, Luca Pignataro, Johannes G de Vries, Umberto Piarulli, Cesare Gennari, Laurent Lefort

Affiliations

  1. DSM Ahead R&D B.V.-Innovative Synthesis, P. O. Box 18, 6160 MD, Geleen, The Netherlands.
  2. Dipartimento di Chimica, Università degli Studi di Milano, via C. Golgi?19, 20133, Milan, Italy.
  3. Leibniz-Institut für Katalyse e.V. an der, Universität Rostock, Albert-Einstein-Str.?29a, 18059, Rostock, Germany.
  4. Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell'Insubria, via Valleggio?11, 22100, Como, Italy.
  5. DSM Ahead R&D B.V.-Innovative Synthesis, P. O. Box 18, 6160 MD, Geleen, The Netherlands. [email protected].

PMID: 27140832 DOI: 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 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.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: asymmetric catalysis; homogeneous catalysis; hydrogenation; pyridines; reaction mechanisms

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