A novel integrated bio- and chemocatalytic approach to the de novo catalytic asymmetric synthesis of saccharides has been developed. Acetoxypyranones obtained enantiopure by enzymatic resolution have been shown to undergo highly stereoselective palladium-catalyzed formal O-glycoside bond formation. The combination of these protocols can be applied to the iterative asymmetric catalytic synthesis of saccharides.
Cobalt carbonyl complexes immobilised onto a 'polymerbound triphenylphosphine' solid support are effective and practical catalysts of the Pauson-Khand reaction.
The immobilisation of functionalised alkynes onto 'polymerbound triphenylphosphine', their chemical manipulation and subsequent release has been demonstrated for the first time, thus illustrating that cobalt carbonyl complexes can be used as 'traceless' p-alkyne linkers.
Carbonylcobalt(0) species have been used as linkers between alkynes and a polymer support for the first time. The alkynes may be loaded indirectly onto a phosphine functionalised polymer via their hexacarbonyldicobalt(0) complex, or directly onto a cobalt coated polymer. The alkynes have been released either as alkynes, thus providing a traceless method of immobilising alkynes, or by reaction with an alkene to generate a cyclopentenone via the Pauson-Khand reaction. The cobalt coated polymers produced during this study were shown to catalyse the Pauson-Khand reaction.
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