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A new generation of chiral P,N-ligands using enantiopure propargylamines

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A new generation of chiral P,N-ligands using enantiopure propargylamines

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Samenvatting

Homogeneous catalysis has many applications. Especially asymmetric homogeneous catalysis is really popular at the moment. It is important to have access to single enantiomers of certain compounds, for example in the synthesis of medicines. An important type of catalysts is organo-metal-complexes. These complexes consist of a metal atom that coordinates to organic molecules, ligands.

The purpose of this investigation is the synthesis of a new type of P,N-ligands containing a triazole ring.

The ligands, shown in figure 1, were synthesized in six steps. The first five reactions in the synthesis of chiral ClickPhine ligands are well know and good described in literature. Proline acetylene was obtained in 23% yield starting from Boc-protected L-proline. The last step is the coupling reaction of the amine with phosphorchloride. The ligands obtained are highly moisture and oxygen sensitive. For ligand A a maximum of yield 35% was obtained, for ligand B 99% conversion was observed.

Ligand B was tested in asymmetric hydrogenation, 44% conversion with 8% ee was obtained. This result reveals that the ligand is capable to induce asymmetry although further investigation is necessary.

In order to obtain more chiral P,N-ligands a new method to synthesize propargylic amines enantioselectively was developed. Synthesis of propargylic amines bearing aromatic side-chains was performed in high yields, 62-97%, and with high enantiomeric excess, 74-86%. Many of these products could be re-crystallized giving the single enantiomere.

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OrganisatieHogeschool Utrecht
OpleidingChemie
AfdelingLife Sciences en Chemistry
PartnersVan ‘t Hoff Institute for Molecular Sciences Faculty of Science University of Amsterdam
Jaar2007
TypeBachelor
TaalEngels

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