Asymmetric  Iridium-Catalysed Hydrogenation
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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.

Pher G. AnderssonUppsala University



Asym hydrogen non functionalized olefines
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.


Asym hydrogenation mechanism
Asym hydrogenation, mechanism

Rh

? Ru ?

? Ir ?

Landis & Halpern J. Am. Chem. Soc. 1987, 109, 1746.


Dft study of ir hydrogenation
DFT study of Ir-hydrogenation

B3LYP/LANL2DZ

Chem. Eur. J. 2003, 9, 339.


Computational chemistry
Computational chemistry

axup

eqt-P

eqt-N

Olefin

axdown



Dft results
DFT results

B3LYP/LANL2DZ

Chem. Eur. J. 2003, 9, 339.



Proposed catalytic cycle
Proposed catalytic cycle

Chem. Eur. J. 2003, 9, 339.



New ligand structures
New ligand structures

Synthesis should be:

  • short and efficient

  • allow preparation of both enantiomeres






Substrate study

J. Am. Chem. Soc.2004,126, 14308.


Further improvements of the ligand strucure
Further improvements ofthe ligand strucure

?

?








Ligand synthesis iii1
Ligand synthesis III

Adv.Synth.Cat. 2008, 350, 1168.




Ligand synthesis iv
Ligand synthesis IV

Org.Lett. 2004, 6, 3825. Chem. Eur. J. 2006, 12, 2318.


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