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

Abstract

[EN] 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.