TitleIntramolecular Pyridinium Oxide Cycloadditions: Systematic Study of Substitution, Diastereoselectivity, and Regioselectivity.
Publication TypeJournal Article
Year of Publication2021
AuthorsLu Y, Dey PN, Beaudry CM
JournalChemistry
Volume27
Issue12
Pagination4028-4032
Date Published2021 Feb 24
ISSN1521-3765
Abstract

Intramolecular pyridinium oxide cycloadditions form complex polycyclic nitrogenous architectures. The diastereoselectivity and regioselectivity of pyridinium oxide cycloadditions was systematically investigated for the first time using complex substrates. Predictably high levels of diastereoselectivity and regioselectivity are observed, which can be attributed to minimization of steric (syn-pentane) and torsional strain in the products. The reaction is reversible under the reaction conditions, and it is stereospecific with respect to the dipolarophile geometry.

DOI10.1002/chem.202100115
Alternate JournalChemistry
PubMed ID33434367
Grant ListCHE-1956401 / / Division of Chemistry /