In summary, we report the first enantioselective synthesis of 1sulfonylcyclopropanols, which constitute versatile precursors to highly energetic chiral cyclopropanone derivatives. Kinetic studies revealed the modular nature of these compounds with respect to their equilibration to cyclopropanones, where both the electronic and steric properties of the sulfinate group can readily be tuned to control their overall reactivity as cyclopropanone equivalents. Such a tunability should prove highly beneficial in future reaction development, allowing different sets of reaction conditions to be compatible with these cyclopropanone surrogates. To showcase their applicability in the synthesis of biologically relevant compounds, a mild and stereospecific formal [3+1] cycloaddition with readily available hydroxylamines was developed, efficiently affording a variety of chiral β-lactam derivatives. All synthetic methods developed herein were shown to proceed with similar efficiency on gram scale, and the use of an enantioenriched cyclopropanone equivalent led to complete transfer of the stereochemical information to the final β-lactam product. To the best of our knowledge, this work constitutes the first general enantioselective approach to cyclopropanone derivatives. Considering the importance of strained ketone rearrangements in synthesis 1 and the tremendous potential of cyclopropanones as reactive intermediates, 4 this work should find widespread use in the elaboration of complex, biologically relevant molecules. The development of various other transformations using 1-sulfonylcyclopropanols as cyclopropanone surrogates is currently underway in our laboratories and will be reported in due course.