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Formation of spirocyclic compounds from heck cyclizations invoking cyclic enamides
, M.E. Maier
Published in
2008
Volume: 73
   
Issue: 14
Pages: 5410 - 5415
Abstract
(Chemical Equation Presented) The palladium-mediated transformation of 3,4-dihydro-2(1H)-pyridinones 12 featuring a (2-bromophenyl)ethyl substituent in the 5-position produces spirocyclic products, imides 14 and amides 15. The formation of these products can be explained by insertion of the enamide double bond into the initial aryl-Pd bond followed by oxidation or reduction of the organopalladium intermediate. Alternatively, formation of these spiro compounds might proceed via acyliminium ion intermediates. © 2008 American Chemical Society.
About the journal
JournalJournal of Organic Chemistry
ISSN00223263