AbstractRacemic and enantiomerically enriched methyl 2‐siloxycyclopropanecarboxylates 1 have been ring‐opened to furnish γ‐oxo esters 2. Depending on the electronic properties of substituents, these could be transformed into either succinate derivatives 3 or 3‐oxybutanoates 4 by Baeyer‐Villiger oxidation. By comparison with known reference compounds the absolute configurations of 3a and 4d, and hence those of their cyclopropane precursors, could be determined. Further literature data on the optical rotations of related cyclopropanes have been collected and compared. A mechanistic interpretation of the asymmetric cyclopropanation of silyl enol ethers based on Pfaltz's model is suggested.