@article{jang_deng_sprague_lindsay_2023, title={Divergent Synthesis of & beta;-Fluoroamides via Silver-Catalyzed Oxidative Deconstruction of Cyclopropanone Hemiaminals}, volume={7}, ISSN={["1523-7052"]}, url={https://doi.org/10.1021/acs.orglett.3c01992}, DOI={10.1021/acs.orglett.3c01992}, abstractNote={An expedient approach for the synthesis of challenging β-fluoroamides from readily accessible cyclopropanone equivalents is reported. Following the addition of pyrazole used here as a transient leaving group, silver-catalyzed regiospecific ring-opening fluorination of the resulting hemiaminal leads to a β-fluorinated N-acylpyrazole intermediate reactive to substitution with amines, ultimately affording β-fluoroamides. The process could also be extended to the synthesis of β-fluoroesters and γ-fluoroalcohols via the addition of alcohols or hydrides as terminal nucleophiles, respectively.}, journal={ORGANIC LETTERS}, author={Jang, Yujin and Deng, Weixia and Sprague, Ivan S. S. and Lindsay, Vincent N. G.}, year={2023}, month={Jul} } @article{jang_machin-rivera_lindsay_2021, title={Synthesis and Applications of Cyclopropanones and Their Equivalents as Three-Carbon Building Blocks in Organic Synthesis}, volume={5}, ISSN={["1437-210X"]}, url={https://doi.org/10.1055/a-1519-1670}, DOI={10.1055/a-1519-1670}, abstractNote={Abstract}, journal={SYNTHESIS-STUTTGART}, publisher={Georg Thieme Verlag KG}, author={Jang, Yujin and Machin-Rivera, Roger and Lindsay, Vincent N. G.}, year={2021}, month={May} } @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} }