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A Proline-Squaraine Ligand Framework (Pro-SqEB) for Stereoselective Rhodium(II)-Catalyzed Cyclopropanations

https://doi.org/10.1021/acs.orglett.3c03344

Bacher, Emily P.; Twiringiyimana, Raïssa; Rodriguez, Kevin X.; Wilson, Renita A.; Bodnar, Alexandra K.; O’Connell, Ryan; Toni, Tiffany A.; Eckert, Kaitlyn E.; Wiest, Olaf; Ashfeld, Brandon L. (November 2023, Organic Letters)

A proline-squaraine ligand (Pro-SqEB) that demonstrates high levels of stereoselectivity in olefin cyclopropanations when anchored to a Rh2 II scaffold is introduced. High yields and enantioselectivities were achieved in the cyclopropanation of alkenes with diazo compounds in the presence of Rh2(Pro- SqEB)4. Notably, the unique electronic and steric design of this catalyst enabled the use of polar solvents that are otherwise incompatible with most RhII complexes.
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Front Cover: Rational Design and Identification of Harmine‐Inspired, N ‐Heterocyclic DYRK1A Inhibitors Employing a Functional Genomic In Vivo Drosophila Model System (ChemMedChem 4/2022)

https://doi.org/10.1002/cmdc.202200066

Huizar, Francisco J.; Hill, Harrison M.; Bacher, Emily P.; Eckert, Kaitlyn E.; Gulotty, Eva M.; Rodriguez, Kevin X.; Tucker, Zachary D.; Banerjee, Monimoy; Liu, Haining; Wiest, Olaf; et al (February 2022, ChemMedChem)

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Aroyl Isocyanates as 1,4-Dipoles in a Formal [4 + 1]-Cycloaddition Approach toward Oxazolone Construction

https://doi.org/10.1021/acs.orglett.8b00656

Eckert, Kaitlyn E.; Ashfeld, Brandon L. (April 2018, Organic Letters)

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A Phosphorus(III)‐Mediated (4+1)‐Cycloaddition of 1,2‐Dicarbonyls and Aza‐ o ‐Quinone Methides to Access 2,3‐Dihydroindoles

https://doi.org/10.1002/hlca.201900192

Eckert, Kaitlyn E.; Lepore, Antonio J.; Ashfeld, Brandon L. (December 2019, Helvetica Chimica Acta)

Abstract A (4+1)‐cycloaddition is reported between 1,2‐dicarbonyls and aza‐o‐quinone methide precursors to access 2,3‐dihydroindoles bearing a tetra‐substituted carbon center. The utilization of dioxyphospholenes as carbene surrogates provided dihydroindoles in 20–90 % yield, wherein the electronic nature of the dioxyphospholene impacts its role in the reaction.
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