The one-pot multistep enzymatic oxidation of aliphatic and benzylic alcohols to the corresponding aldehydes combined with their subsequent carboligation to chiral α-hydroxy ketones has been exemplarily evaluated in terms of being a “green” biocatalytic approach. Besides the potential to start from bio-derived alcohols, this concept avoids the direct use of the reactive aldehyde intermediates, enables addition of high substrate concentrations in one liquid phase while maintaining enzyme activity and enables a simplified product isolation with diminished waste formation.