How can a ketone be enantioselectively reduced, in the presence of an ester?
I have had great results for enantioselective ketone reduction using the Noyori Ru-TsDPEN system.
This has advantages through being catalytic with low stoichiometry and doesn't require high pressure, or molecular hydrogen for that matter. The downside might be the initial cost of the catalyst / chiral ligand but you don't need very much. The typical reduction reagents are triethylamine and formic acid, making this a very mild system to work with in terms of conditions.
It might be cheaper to purchase the RuCl2(p-cymene) and chiral TsDPEN separately. That way you can also play with the ligand-metal ratio if you need to.
This saves a lot of hassle rather than adding on and removing chiral auxiliaries