Boron-tethered oxidopyrylium-based [5 + 2] cycloadditions

Corrie, Seth I.; Pearce, Aaron C.; Grabowski, Jacob P.; Randolph, Kee A.; Guo, Wentao; Tantillo, Dean J.; Mitchell, T. Andrew

doi:10.1016/j.tetlet.2022.154094

Tetrahedron Letters

2022

DOI: 10.1016/j.tetlet.2022.154094

|View full text |Cite

Boron-tethered oxidopyrylium-based [5 + 2] cycloadditions

Seth I. Corrie

Aaron C. Pearce²,

Jacob P. Grabowski³

et al.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2023

Publication Types

Select...

Article2

Relationship

Self Cite1

Independent1

Authors

Journals

Cited by 2 publications

(1 citation statement)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A detailed computational study was undertaken to investigate these amide-tethered cycloadditions in comparison to previous carbon-tethered variants. , Initial conformational searches were carried out using CREST, and subsequent DFT calculations were carried out with Gaussian16 . The M06-2X functional with D3(0) dispersion correction was used to locate stationary points, because this functional is known to perform well for main group thermochemistry and kinetic studies .…”

mentioning

confidence: 99%

Net Intermolecular Silyloxypyrone-Based (5+2) Cycloadditions Utilizing Amides as Enabling and Cleavable Tethers

Angles,

Guo,

Darko

et al. 2023

Org. Lett.

View full text Add to dashboard Cite

mentioning

confidence: 99%

Net Intermolecular Silyloxypyrone-Based (5+2) Cycloadditions Utilizing Amides as Enabling and Cleavable Tethers

Angles,

Guo,

Darko

et al. 2023

Org. Lett.

View full text Add to dashboard Cite

Experimental and Theoretical Investigation of the Synchronicity of Ambident Silyloxypyrone-Based (5 + 2) Cycloadditions

et al. 2023

Self Cite

View full text Add to dashboard Cite

The reaction pathway of silyloxypyrone-based (5 + 2) cycloadditions was determined to be extremely dependent on the nature of the dipolarophile. Neutral alkenes were the least reactive, whereas both electron-deficient and electron-rich dipolarophiles were more reactive, thus providing evidence for ambident oxidopyrylium intermediates. Qualitative rate studies, Hammett linear free energy relationships, and theoretical calculations combined to provide evidence for a spectrum of reactivity that passes through the borderlands of concerted and stepwise.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

hi@scite.ai

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Boron-tethered oxidopyrylium-based [5 + 2] cycloadditions

Cited by 2 publications

References 42 publications

Net Intermolecular Silyloxypyrone-Based (5+2) Cycloadditions Utilizing Amides as Enabling and Cleavable Tethers

Net Intermolecular Silyloxypyrone-Based (5+2) Cycloadditions Utilizing Amides as Enabling and Cleavable Tethers

Experimental and Theoretical Investigation of the Synchronicity of Ambident Silyloxypyrone-Based (5 + 2) Cycloadditions

Contact Info

Product

Resources

About