Alkenes enantioselectivities

Shibasaki, M., VogI, E. M. The palladium-catalyzed arylation and vinylation of alkenes-enantioselective fashion. J. Organomet. Chem. 1999,576, 1-15. 

Making the other diastereoisomer would require the cis alkene. This is not a problem in itself, but more of a challenge for the catalyst, because now it has to distinguish between two similar groups (Et and Me) in order to oxidize one face of the alkene enantioselectively (for the trans alkene, the selection is between either Et and H or Me and H switching Et for Me makes no difference to the outcome). 

Table 8.2 Alkene enantioselective hydroformylation with Rh/P-stereogenic ligands. 

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