Diastereoisomeric enrichment of 1,4-enediols and H-2-splitting inhibition on Pd-supported catalysts

Pd-supported catalysts are fundamental tools in organic reactions involving H-2 splitting. Here we show that 1,4-enediols enriched in one diastereoisomer are produced from the classical Pd-catalyzed semi-hydrogenation reaction with H-2, starting from the corresponding, widely available 1,4-diacetylenic diols. The semi-hydrogenation reaction proceeds concomitantly with the desymmetrization of the meso/racemic form of the enediol. We also show that these products, if added in advance to H-2, completely inactivate the Pd catalyst (only when added before H-2). These results provide a simple way not only to produce 1,4-enediols enriched in one diastereoisomer by a classical catalytic method but also to stop H-2 dissociation on Pd nanoparticles.

Automated summary

This study demonstrates the synthesis of 1,4-enediols enriched in one diastereoisomer through the classical Pd-catalyzed semi-hydrogenation reaction using readily available 1,4-diacetylenic diols. The semi-hydrogenation reaction concurrently involves the desymmetrization of the meso/racemic form of the enediol. Additionally, it is found that these products can completely inactivate the Pd catalyst when added to H-2 in advance (only before H-2). These findings not only provide a straightforward method for the production of 1,4-enediols enriched in one diastereoisomer using classical catalysis but also offer a means to inhibit H-2 dissociation on Pd nanoparticles.