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A series of 16 different 3‐acyloxy methyl ketones, the acyloin acetates and butyrates (±)‐5 , was synthesised by a straightforward new method through alkylation of tert‐butyl 2‐acyloxyacetoacetates 3 , followed by chemoselective dealkoxycarbonylation of the tert‐butyloxycarbonyl group in the presence of other ester groups. Subsequent hydrolysis of (±)‐5 can be achieved with base to give racemic acyloins 6 , or with lipase catalysis to afford the corresponding non‐racemic acyloins (S )‐6 . The remaining (R )‐acyloin esters 5 can be racemised and resubjected to the procedure, or hydrolysed chemically. The kinetic resolution with two of the six tested enzymes, CAL‐B and BCL (PS) lipase, proceeded selectively [enantiomeric ratio (E ) values between 50 and > 200] and most of the acyloins (S )‐6 were obtained in very high enantiomeric excesses (up to > 99% ee ).