Intramolecular Pd-catalyzed aryl-enone conjugate additions. Control of reductive vs non-reductive cyclization

Gregory K. Friestad, Bruce P. Branchaud

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Abstract

Pd-catalyzed aryl-enone cyclization of 1 leads to Heck-type non-reductive cyclization product 3 and reductive cyclization product 4. Conditions have been developed to selectively form either 3 or 4 (or more highly functionalized 10 vs 11 or 13 vs 14). The formation of non-reductive cyclization products (3, 11, 14) requires an unusual apparent trans β-H elimination - some mechanistic possibilities that are consistent with the data are proposed.

Original languageEnglish (US)
Pages (from-to)7047-7050
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number39
DOIs
StatePublished - Sep 25 1995

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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