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    J Org Chem. 2008 Sep 19;73(18):7080-7. Epub 2008 Aug 26.

    N-phosphino-p-tolylsulfinamide ligands: synthesis, stability, and application to the intermolecular Pauson-Khand reaction.

    Source

    Unitat de Recerca en Síntesi Asimètrica (URSA-PCB), Institute for Research in Biomedicine, Universitat de Barcelona, c/Baldiri Reixac 10, E-08028 Barcelona, Spain.

    Abstract

    Here we synthesized a family of racemic and optically pure N-phosphino-p-tolylsulfinamide (PNSO) ligands. Their stability and coordination behavior toward dicobalt-alkyne complexes was evaluated. Selectivities of up to 3:1 were achieved in the ligand exchange process with (mu-TMSC2H)Co2(CO)6. The resulting optically pure major complexes were tested in the asymmetric intermolecular Pauson-Khand reaction and yielded up to 94% ee. X-ray studies of the major complex 18a indicated that the presence of an aryl group on the sulfinamide reduces the hemilabile character of the PNSO ligands.

    PMID:
    18729408
    [PubMed - indexed for MEDLINE]

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