@misc{poteat_lindsay_2021, title={Stereospecific Synthesis of Enantioenriched Alkylidenecyclobutanones via Formal Vinylidene Insertion into Cyclopropanone Equivalents}, volume={23}, ISSN={["1523-7052"]}, url={https://doi.org/10.1021/acs.orglett.1c02303}, DOI={10.1021/acs.orglett.1c02303}, abstractNote={1-Sulfonylcyclopropanols are employed here as efficient cyclopropanone equivalents in a formal vinylidene insertion process, providing the first general synthetic route to enantioenriched alkylidenecyclobutanones. The addition of an alkenyl-Grignard reagent leads to an alkenylcyclopropanol capable of electrophilic activation by N-bromosuccinimide, triggering a regio- and stereospecific 1,2-migration and affording alkylidenecyclobutanones after elimination. Activation of the intermediate with other electrophiles such as HCl or mCPBA leads to the formation of various chiral cyclobutanones and γ-lactones via alternative pathways.}, number={16}, journal={ORGANIC LETTERS}, publisher={American Chemical Society (ACS)}, author={Poteat, Christopher M. and Lindsay, Vincent N. G.}, year={2021}, month={Aug}, pages={6482–6487} } @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} } @article{rivera_jang_poteat_lindsay_2020, title={General Synthesis of Cyclopropanols via Organometallic Addition to 1-Sulfonylcyclopropanols as Cyclopropanone Precursors}, volume={22}, ISSN={1523-7060 1523-7052}, url={http://dx.doi.org/10.1021/acs.orglett.0c02303}, DOI={10.1021/acs.orglett.0c02303}, abstractNote={The addition of organometallic reagents to ketones constitutes one of the most straightforward synthetic approaches to tertiary alcohols. However, due to the absence of a well-behaved class of cyclopropanone surrogates accessible in enantioenriched form, such a trivial synthetic disconnection has received very little attention in the literature for the formation of tertiary cyclopropanols. In this work, we report a simple and high-yielding synthesis of 1-substituted cyclopropanols via the addition of diverse organometallic reagents to 1-phenylsulfonylcyclopropanols, acting here as in situ precursors of the corresponding cyclopropanones. The transformation is shown to be amenable to sp-, sp2-, or sp3-hybridized organometallic C-nucleophiles under mild conditions, and the use of enantioenriched substrates led to highly diastereoselective additions and the formation of optically active cyclopropanols.}, number={16}, journal={Organic Letters}, publisher={American Chemical Society (ACS)}, author={Rivera, Roger Machín and Jang, Yujin and Poteat, Christopher M. and Lindsay, Vincent N. G.}, year={2020}, month={Aug}, pages={6510–6515} } @article{poteat_lindsay_2019, title={Controlled -mono- and ,-di-halogenation of alkyl sulfones using reagent-solvent halogen bonding}, volume={55}, ISSN={["1364-548X"]}, url={https://doi.org/10.1039/C9CC00550A}, DOI={10.1039/c9cc00550a}, abstractNote={The direct and selective α-halogenation of alkyl sulfones was achieved via base-mediated electrophilic halogenation, where reagent–solvent halogen bonding was found to control the selectivity through alteration of the effective size of the halogen source.}, number={20}, journal={CHEMICAL COMMUNICATIONS}, publisher={Royal Society of Chemistry (RSC)}, author={Poteat, Christopher M. and Lindsay, Vincent N. G.}, year={2019}, month={Mar}, pages={2912–2915} }