@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}, 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 Cyclopropanone derivatives constitute highly strained cycloalkanones with promising applications as three-carbon building blocks in organic synthesis. Due to the presence of a ketone in such a small ring system, all C–C bonds and the carbonyl group are considered to be labile in suitable conditions, leading to a wide variety of synthetic disconnections, including nucleophilic addition, ring expansion, ring-opening, and (formal) cycloaddition. Despite their synthetic potential, the widespread adoption of cyclopropanones as substrates has been considerably hampered by the difficulties associated with the preparation and storage of such unstable compounds, prompting the development of cyclopropanone surrogates that can equilibrate to the parent ketone in situ via elimination. This review summarizes the syntheses and applications of cyclopropanone derivatives and their equivalents, and offers a perspective of the state of the field as well as its expected future directions. 1 Introduction 2 Preparation of Cyclopropanones and Their Equivalents 2.1 Carbenoid Chemistry 2.2 Allene Oxide Rearrangement 2.3 Ring Closure by Dehydrohalogenation or Dehalogenation 2.4 Photolytic Processes 2.5 Miscellaneous Formation of Cyclopropanones 2.6 Cyclopropanone Equivalents 3 Synthetic Applications of Cyclopropanones and Their Equivalents 3.1 Nucleophilic Addition to the Carbonyl Group 3.2 Ring Expansion 3.3 Ring-Opening 3.4 Cycloaddition and Formal Cycloaddition 4 Conclusion and Outlook}, 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 Cyclopropanone derivatives have long been considered unsustainable synthetic intermediates because of their extreme strain and kinetic instability. Reported here is the enantioselective synthesis of 1‐sulfonylcyclopropanols, as stable yet powerful equivalents of the corresponding cyclopropanone derivatives, by α‐hydroxylation of sulfonylcyclopropanes using a bis(silyl) peroxide as the electrophilic oxygen source. This work constitutes the first general approach to enantioenriched cyclopropanone derivatives. Both the electronic and steric nature of the sulfonyl moiety, which serves as a base‐labile protecting group and confers crystallinity to these cyclopropanone precursors, were found to have a crucial impact on the rate of equilibration to the corresponding cyclopropanone. The utility of these cyclopropanone surrogates is demonstrated in a mild and stereospecific formal [3+1] cycloaddition with simple hydroxylamines, leading to the efficient formation of chiral β‐lactam derivatives.}, 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} }