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Phosphane Sulfide/Octacarbonyldicobalt-Catalyzed Pauson - Khand Reaction Under an Atmospheric Pressure of Carbon Monoxide.

Angew Chem Int Ed Engl

February 2000

Department of Chemistry and Biotechnology Graduate School of Engineering, The University of Tokyo Hongo, Tokyo 113-8656 (Japan).

Convenient access to cyclopentenones is provided by catalytic intra- and intermolecular Pauson - Khand reactions in the presence of octacarbonyldicobalt and tributylphosphane sulfide (see scheme). In contrast to other reactions of this type, they proceed under mild conditions (70 degrees C, 1 atm CO), and commercially available [Co(2)(CO)(8)] can be used without further purification.

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A catalytic version has now been developed for the enantioselective total synthesis of epothilone A (1). The key is the use of multifunctional asymmetric catalyses for a direct aldol reaction and cyanosilylation. This successful approach demonstrated the usefulness of these reactions for the catalytic asymmetric synthesis of complex molecules.

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