Enantioselective reductions are a key to successful target-oriented syntheses. Finding the most suitable conditions is often a tedious work that is especially hampered by the time-consuming analytical investigation. A possible solution is the combined use of high-performance liquid chromatography and circular dichroism to find a suitable system for providing enantiomerically pure alcohols. This investigation led to an efficient protocol for the alcohol dehydrogenase-catalyzed reduction of 1-phenyl-2-propyn-3-trimethylsilyl-1-on (). Chirality, 2011. © 2011Wiley Periodicals, Inc.