Directed hydrozirconation of homopropargylic alcohols

Xiaofeng Liu, Joseph M. Ready

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Homopropargylic alcohols undergo directed hydrozirconation with Schwartz reagent (Cp2ZrHCl) to generate vinyl-metal species in which the metal fragment is proximal to the alkoxide. Electrophilic trapping yields tri-substituted olefins in good yields with good control of regio- and stereochemistry. Experiments with a homopropargylic ether confirmed the role of the hydroxyl group in the directed hydrometalation.

Original languageEnglish (US)
Pages (from-to)6955-6960
Number of pages6
JournalTetrahedron
Volume64
Issue number29
DOIs
StatePublished - Jul 14 2008

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Metals
Alcohols
Stereochemistry
Alkenes
Hydroxyl Radical
Ether
Experiments
Schwartz reagent

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Directed hydrozirconation of homopropargylic alcohols. / Liu, Xiaofeng; Ready, Joseph M.

In: Tetrahedron, Vol. 64, No. 29, 14.07.2008, p. 6955-6960.

Research output: Contribution to journalArticle

Liu, Xiaofeng ; Ready, Joseph M. / Directed hydrozirconation of homopropargylic alcohols. In: Tetrahedron. 2008 ; Vol. 64, No. 29. pp. 6955-6960.
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