Palladium-catalyzed regiocontrolled and stereoselective alkylations of bis(trifluoroethyl) malonates with dienyl alcohols

James M. Takacs, Xun Tian Jiang, Alexei P. Leonov

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The triethylborane-promoted and palladium-catalyzed reactions of 2, 4-dienyl alcohols or the corresponding isomeric divinyl alcohols with bis(trifluoroethyl) malonates provide an improved method for the regio- and stereoselective dienylation of malonates. The phosphine ligand is an important control element in the reaction. Combinations of Pd(OAc)2 with BIPHEP or BINAP give dienylated malonates in good yield and higher isomeric purity than the traditional combination of Pd(OAc)2 and Ph 3P affords in the catalyzed reactions of dienyl acetates.

Original languageEnglish (US)
Pages (from-to)7075-7079
Number of pages5
JournalTetrahedron Letters
Volume44
Issue number37
DOIs
StatePublished - Sep 8 2003

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Malonates
Alkylation
Palladium
phosphine
Alcohols
Acetates
Ligands
palladium(II) acetate

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Palladium-catalyzed regiocontrolled and stereoselective alkylations of bis(trifluoroethyl) malonates with dienyl alcohols. / Takacs, James M.; Jiang, Xun Tian; Leonov, Alexei P.

In: Tetrahedron Letters, Vol. 44, No. 37, 08.09.2003, p. 7075-7079.

Research output: Contribution to journalArticle

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