@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={https://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} } @article{jung_lindsay_2022, title={One-Pot Synthesis of Strain-Release Reagents from Methyl Sulfones br}, volume={144}, ISSN={["1520-5126"]}, url={https://doi.org/10.1021/jacs.2c00923}, DOI={10.1021/jacs.2c00923}, abstractNote={Sulfone-substituted bicyclo[1.1.0]butanes and housanes have found widespread application in organic synthesis due to their bench stability and high reactivity in strain-releasing processes in the presence of nucleophiles or radical species. Despite their increasing utility, their preparation typically requires multiple steps in low overall yield. In this work, we report an expedient and general one-pot procedure for the synthesis of 1-sulfonylbicyclo[1.1.0]butanes from readily available methyl sulfones and inexpensive epichlorohydrin via the dialkylmagnesium-mediated formation of 3-sulfonylcyclobutanol intermediates. Furthermore, the process was extended to the formation of 1-sulfonylbicyclo[2.1.0]pentane (housane) analogues when 4-chloro-1,2-epoxybutane was used as the electrophile instead of epichlorohydrin. Both procedures could be applied on a gram scale with similar efficiency and are shown to be fully stereospecific in the case of housanes when an enantiopure epoxide was employed, leading to a streamlined access to highly valuable optically active strain-release reagents.}, number={11}, journal={JOURNAL OF THE AMERICAN CHEMICAL SOCIETY}, publisher={American Chemical Society (ACS)}, author={Jung, Myunggi and Lindsay, Vincent N. G.}, year={2022}, month={Mar}, pages={4764–4769} } @article{poteat_jang_jung_johnson_williams_lindsay_2020, title={Enantioselective Synthesis of Cyclopropanone Equivalents and Application to the Formation of Chiral β-Lactams}, volume={59}, ISSN={["1521-3773"]}, url={https://doi.org/10.1002/anie.202006786}, DOI={10.1002/anie.202006786}, abstractNote={Abstract}, number={42}, journal={Angewandte Chemie International Edition}, publisher={Wiley}, author={Poteat, C.M. and Jang, Y. and Jung, M. and Johnson, J.D. and Williams, R.G. and Lindsay, V.N.G.}, year={2020}, pages={18655–18661} }