Stereoelectronic Model To Explain Highly Stereoselective Reactions of Seven-Membered-Ring Oxocarbenium-Ion Intermediates

Angewandte Chemie
Matthew G BeaverK A Woerpel

Abstract

Nucleophilic attack on seven-membered-ring oxocarbenium ions is generally highly stereoselective. The preferred mode of nucleophilic attack forms the product in a conformation that minimizes transannular interactions, thus leading to different stereoselectivity as compared to that of reactions involving six-membered-ring oxocarbenium ions.

References

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Citations

Apr 9, 2021·Beilstein Journal of Organic Chemistry·Anthony J FernandesSébastien Thibaudeau
May 26, 2021·The Journal of Organic Chemistry·Emanuele CasaliGiuseppe Zanoni
Aug 8, 2019·Journal of the American Chemical Society·Laura Montalvillo-JiménezJuan Luis Asensio
Jun 25, 2020·Journal of the American Chemical Society·Andrés G SantanaJuan Luis Asensio

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