Manufacture of Asymmetric Hydrogenation Catalysts - Pharmaceutical Technology

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Manufacture of Asymmetric Hydrogenation Catalysts
Single-enantiomer drugs represent an increasingly large share of new chemical entities, leading to approaches in asymmetric synthesis.


Pharmaceutical Technology


Ian C. Lennon*, PhD, is a scientist and technology leader, Nicholas B. Johnson, PhD, is a business development and marketing manager, and Paul H. Moran, PhD, is a research specialist at Chirotech Technology Ltd., Dowpharma, Unit 162, Cambridge Science Park, Milton Road, Cambridge, UK, tel. + 44 (0) 1223.728037, fax +44 (0)1223.506701
.

*To whom all correspondence should be addressed.

References

1. W.S. Knowles, "Asymmetric Hydrogenations," Angew Chem. Int. Ed. 41 (12), 1998–2007 (2002).

2. R. Noyori, Asymmetric Catalysis in Organic Synthesis (John Wiley & Sons Inc, New York, 1994).

3. M.A. Schwindt et al., "Enantioselective Synthesis of a Key Intermediate in a New Process for Orlistat Using Asymmetric Hydrogenation and a Grignard Reagent Promoted Lactone Cyclization," Org. Process Res. Dev. 11 (3), 524–533 (2007).

4. M.J. Burk, "Modular Phospholane Ligands in Asymmetric Catalysis," Acc. Chem. Res. 33 (6), 363–372 (2000).

5. A. Togni et al., "A Novel Easily Accessible Chiral Ferrocenyldiphosphine for Highly Enantioselective Hydrogenation, Allylic Alkylation, and Hydroboration Reactions," J. Am. Chem. Soc. 116 (9), 4062–4066 (1994).

6. H.U. Blaser, "The Chiral Switch of (S)-Metolachlor: A Personal Account of an Industrial Odyssey in Asymmetric Catalysis," Adv. Synth. Catal. 344 (1), 17–31 (2002).

7. I.C. Lennon and C.J. Pilkington, "The Application of Asymmetric Hydrogenation for the Manufacture of Pharmaceutical Intermediates: The Need for Catalyst Diversity," Synthesis (11), 1639–1642 (2003).

8. W. Tang and X. Zhang, "New Chiral Phosphorus Ligands for Enantioselective Hydrogenation," Chem. Rev. 103 (8) 3029–3069 (2003).

9. T.Yamano et al., "Approach to the Stereoselective Synthesis of Melatonin Receptor Agonist Ramelteon via Asymmetric Hydrogenation," Tetrahedron: Asymmetry 17 (2), 184–190 (2002).

10. Y. Hsiao et al., "Highly Efficient Synthesis of β-Amino Acid Derivatives via Asymmetric Hydrogenation of Unprotected Enamines," J. Am. Chem. Soc. 126 (32), 9918–9919 (2004).

11. J.A.F. Boogers et al., "A Mixed-Ligand Approach Enables the Asymmetric Hydrogenation of an α-Isopropylcinnamic Acid en Route to the Renin Inhibitor Aliskiren," Org. Process Res. Dev. 11 (3), 585–591.

12. C. Cobley et al., "The Application of DuPHOS Rhodium(I) Catalysts for Commercial Scale Asymmetric Hydrogenation" in Asymmetric Catalysis on Industrial Scale, H.U. Blaser and E. Schmidt, Eds. (Wiley–VCH, Weinheim, Germany, 2004), p. 269–282.

13. M.J. Burk et al., "Practical Access to 2-Alkylsuccinates through Asymmetric Catalytic Hydrogenation of Stobbe-Derived Itaconates," Angew. Chem. Int. Ed., 37 (13–14), 1931–1933 (1998).


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