This is en example of what we learned in class, the Markovnikov hydration of n-propyne (a terminal Alkyne) that produces a Ketone. Using ACS publications, i found an article that describes an ideal anti-Markovnikov hydration of the same compound, to produce an Aldehyde instead.

To induce this reaction, the catalyst cyclopentadienylruthenium is used in a 2-Propanol solvent at 100 deg C, with yields over 99% for this reaction, other Alkynes bearing over 90% for the most part.

The above is one of the final reactions in the synthesis of an enantiospecifically labeled fatty acid. It involves a reduction with Lindlar’s Catalyst in the presence of deuterium, an isotope of hydrogen. Lindlar’s Catalyst (powdered barium sulfate coated with Pd, poisoned with quinoline) converts an alkyne to a cis-alkene, as seen in the reaction above. The article I looked at focused on pheromone biosynthesis in S. isatideus and the role stereochemistry played.