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Under Pressure: Rapid Development of Scalable Asymmetric Hydrogenation Catalysts

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Abstract

Catalytic asymmetric hydrogenation is arguably one of most efficient methods of choice to synthesize a stereogenic center. The time to market pressure and the wide diversity of possible compounds require a flexible and rapid approach to implement technology. The automated synthesis and screening protocol of monodentate ligands, developed at DSM, provides such a technology. Applications of this, so-called, MonoPhosTM ligand library in Rh- and Ir-catalyzed asymmetric hydrogenations have led to cost-effective productions of intermediates for several drugs, such as Aliskiren. A new bulky phosphite ligand has been identified performing particularly well for the asymmetric hydrogenation of the sterically demanding enamide 5.

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Notes

  1. DSM has a non-exclusive license from the Max Planck Institute in Mülheim an den Ruhr, Germany, for the use of monodentate phosphites in asymmetric hydrogenation processes.

  2. TOF stands for turn over frequency. Sampling overnight showed a >99% conversion.

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Acknowledgments

Thanks to Merck & Co. for the collaboration and the permission to disclose our results obtained for the asymmetric hydrogenation of compound 5.

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Authors and Affiliations

  1. DSM Pharmaceutical Products—Innovative Synthesis and Catalysis, PO Box 18, 6160, MD, Geleen, The Netherlands

    Laurent Lefort, Jeroen A. F. Boogers, Johannes G. de Vries & André H. M. de Vries

Authors
  1. Laurent Lefort
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  2. Jeroen A. F. Boogers
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  3. Johannes G. de Vries
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  4. André H. M. de Vries
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Corresponding author

Correspondence to André H. M. de Vries.

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Lefort, L., Boogers, J.A.F., de Vries, J.G. et al. Under Pressure: Rapid Development of Scalable Asymmetric Hydrogenation Catalysts. Top Catal 53, 1081–1086 (2010). https://doi.org/10.1007/s11244-010-9536-2

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  • DOI: https://doi.org/10.1007/s11244-010-9536-2

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