J
Joel L. Mackey
Researcher at University of California, Los Angeles
Publications - 7
Citations - 821
Joel L. Mackey is an academic researcher from University of California, Los Angeles. The author has contributed to research in topics: Aryne & Cycloaddition. The author has an hindex of 6, co-authored 7 publications receiving 730 citations.
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Journal ArticleDOI
Reactivity of biarylazacyclooctynones in copper-free click chemistry
Chelsea G. Gordon,Joel L. Mackey,John C. Jewett,Ellen M. Sletten,Kendall N. Houk,Carolyn R. Bertozzi +5 more
TL;DR: A systematic analysis of the effects of strain and electronics on the reactivity of cyclooctynes with azides through both experimental measurements and computational studies using a density functional theory (DFT) distortion/interaction transition state model suggests a correlation between decreased alkyne bond angle and increasedcyclooctyne reactivity.
Journal ArticleDOI
The role of aryne distortions, steric effects, and charges in regioselectivities of aryne reactions.
TL;DR: These efforts show that aryne distortion, rather than steric factors or charge distribution, are responsible for the regioselectivities observed in 3-haloaryne trapping experiments, and demonstrate the synthetic utility of 3-halobenzynes for the efficient synthesis of functionalized heterocycles.
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Control and design of mutual orthogonality in bioorthogonal cycloadditions.
TL;DR: Two new bioorthogonal reagents, methylcyclopropene and 3,3,6,6-tetramethylthiacycloheptyne, are predicted to be mutually orthogonal in azide and tetrazine cycloadditions.
Journal ArticleDOI
Steric Effects Compete with Aryne Distortion to Control Regioselectivities of Nucleophilic Additions to 3-Silylarynes
TL;DR: Nucleophilic additions to 3-tert-butylbenzyne, which is not significantly distorted, give meta-substituted products, and calculations correctly predict the preferred site of attack observed in both nucleophilic addition and cycloaddition experiments.
Journal ArticleDOI
Origins of Stereoselectivity in the trans-Diels-Alder Paradigm
Robert S. Paton,Joel L. Mackey,Woo Han Kim,Jun Hee Lee,Samuel J. Danishefsky,Kendall N. Houk +5 more
TL;DR: The regioselectivities and stereoselectivity of radical hydrodenitration of the cis-Diels-Alder adduct is found to be related to the relative conformational stabilities of bicyclic radical intermediates.