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Annulated Isoxazoles via [3+2] Cycloaddition of Alkenyl Bromides and Oximoyl Chlorides and Ag(I) Promoted Elimination

TitleAnnulated Isoxazoles via [3+2] Cycloaddition of Alkenyl Bromides and Oximoyl Chlorides and Ag(I) Promoted Elimination
Publication TypeJournal Article
Year of Publication2014
AuthorsCastillo-Contreras, EB, Stahl, AM, Dake, GR
JournalJOURNAL OF ORGANIC CHEMISTRY
Volume79
Pagination7250-7255
Date PublishedAUG 1
ISSN0022-3263
Abstract

Substituted salicylaldehydes are converted to fused tetracyclic isoxazoles through a synthetic sequence incorporating substitution of 2-bromo-2-cyclohexen-1-ol, formation of an oxime function, conversion to an oximoyl chloride, intramolecular {[}3 + 2] cycloaddition, and elimination of an equivalent of hydrogen bromide using silver(I) carbonate. Six examples of this sequence are presented.

DOI10.1021/jo501376q