@article{jung_muir_lindsay_2023, title={Expedient synthesis of spiro[3.3]heptan-1-ones via strain-relocating semipinacol rearrangements}, volume={134}, ISSN={["1464-5416"]}, url={http://dx.doi.org/10.1016/j.tet.2023.133296}, DOI={10.1016/j.tet.2023.133296}, abstractNote={A novel approach for the formation of the highly strained spiro[3.3]heptan-1-one motif was developed through the reaction of 1-sulfonylcyclopropanols and lithiated 1-sulfonylbicyclo[1.1.0]butanes. Following initial nucleophilic addition to the cyclopropanone formed in situ, the resulting 1-bicyclobutylcyclopropanol intermediate is prone to a 'strain-relocating' semipinacol rearrangement in the presence of acid, directly affording the substituted spiro[3.3]heptan-1-one. The process is shown to be fully regio- and stereospecific when starting from a substituted cyclopropanone equivalent, leading to optically active 3-substituted spiro[3.3]heptan-1-ones. The reaction likely proceeds via initial protonation of the bicyclobutyl moiety followed by [1,2]-rearrangement of the resulting cyclopropylcarbinyl cation.}, journal={TETRAHEDRON}, publisher={Elsevier BV}, author={Jung, Myunggi and Muir, Joanna E. and Lindsay, Vincent N. G.}, year={2023}, month={Mar} }