Herein we report on the development and application of chemoenzymatic Dynamic Kinetic Asymmetric Transformation (DYKAT) of alpha-substituted beta-hydroxketones (beta-HKs), using Candida antartica lipase B (CALB) as transesterification catalyst and a ruthenium complex as epimerization catalyst. An operationally simple protocol allows for an efficient preparation of highly enantiomerically enriched alpha-substituted beta-oxoacetates. The products were obtained in yields up to 95% with good diastereomeric ratios.