Surprisingly Mild Enolate-Counterion-Free Pd(0)-Catalyzed Intramolecular Allylic Alkylations

David Madec, Guillaume Prestat, Elisabetta Martini, Peter Fristrup, Giovanni Poli, Per-Ola Norrby

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

Palladium-catalyzed intramolecular allylic alkylations of unsaturated EWG-activated amides can take place under phase-transfer conditions or in the presence of a crown ether. These new reaction conditions are milder and higher yielding than those previously reported. A rationalization for such an unexpected result is put forth and validated by DFT-B3LYP calculations. The results suggest cyclization via a counterion-free (E)-enolate TS.
Original languageEnglish
JournalOrganic Letters
Volume7
Issue number6
Pages (from-to)995-998
ISSN1523-7060
DOIs
Publication statusPublished - 2005

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