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Asymmetric Iridium-Catalysed Hydrogenation New Ligands, New Substrates .

Asymmetric Iridium-Catalysed Hydrogenation New Ligands, New Substrates . Pher G. Andersson Uppsala University. Asym hydrogenation of olefins. Rh Ru. Asym hydrogen non-functionalized olefines. Ru (II) - BINAP. Rh (I) - BINAP. Takaya 1995. Buchwald 1993.

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Asymmetric Iridium-Catalysed Hydrogenation New Ligands, New Substrates .

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  1. Asymmetric Iridium-Catalysed Hydrogenation New Ligands, New Substrates. Pher G. AnderssonUppsala University

  2. Asym hydrogenation of olefins Rh Ru

  3. Asym hydrogen non-functionalized olefines Ru (II) - BINAP Rh (I) - BINAP Takaya 1995 Buchwald 1993 Halterman Comprehensive Asymmetric Catalysis Springer 1999, vol.1, 183-195.

  4. Asym hydrogenation, mechanism Rh ? Ru ? ? Ir ? Landis & Halpern J. Am. Chem. Soc. 1987, 109, 1746.

  5. DFT study of Ir-hydrogenation B3LYP/LANL2DZ Chem. Eur. J. 2003, 9, 339.

  6. Computational chemistry axup eqt-P eqt-N Olefin axdown

  7. X-Ray structure vs DFT

  8. DFT results B3LYP/LANL2DZ Chem. Eur. J. 2003, 9, 339.

  9. DFT results

  10. Proposed catalytic cycle Chem. Eur. J. 2003, 9, 339.

  11. Coupled MI and Ox Add

  12. New ligand structures Synthesis should be: • short and efficient • allow preparation of both enantiomeres

  13. Ligand structure and synthesis

  14. Synthesis

  15. Preparation of catalysts

  16. Evaluation of catalysts

  17. Substrate study J. Am. Chem. Soc.2004,126, 14308.

  18. Further improvements ofthe ligand strucure ? ?

  19. Oxazole vs Thiazole

  20. Ligand synthesis II

  21. Ligand, absolute configuration

  22. Ligand evaluation

  23. Results

  24. Ligand synthesis III

  25. Ligand synthesis III Adv.Synth.Cat. 2008, 350, 1168.

  26. Separation of the enantiomeresby ChiralCel OD

  27. A new class of ligands

  28. Ligand synthesis IV Org.Lett. 2004, 6, 3825. Chem. Eur. J. 2006, 12, 2318.

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