Directed hydrozirconation of homopropargylic alcohols

Xiaofeng Liu; Joseph M. Ready

doi:10.1016/j.tet.2008.03.052

Directed hydrozirconation of homopropargylic alcohols

Xiaofeng Liu, Joseph M. Ready

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

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 language	English (US)
Pages (from-to)	6955-6960
Number of pages	6
Journal	Tetrahedron
Volume	64
Issue number	29
DOIs	https://doi.org/10.1016/j.tet.2008.03.052
State	Published - Jul 14 2008

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2008.03.052

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title = "Directed hydrozirconation of homopropargylic alcohols",

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.",

author = "Xiaofeng Liu and Ready, {Joseph M.}",

note = "Funding Information: We thank Donghui Zhang (UTSW) for key initial experiments. Financial support was provided by the Welch Foundation (I-1612) and the NIH (NIGMS, R01-GM074822). ",

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AU - Liu, Xiaofeng

AU - Ready, Joseph M.

N1 - Funding Information: We thank Donghui Zhang (UTSW) for key initial experiments. Financial support was provided by the Welch Foundation (I-1612) and the NIH (NIGMS, R01-GM074822).

PY - 2008/7/14

Y1 - 2008/7/14

N2 - 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.

AB - 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.

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JO - Tetrahedron

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ER -

Directed hydrozirconation of homopropargylic alcohols

Abstract

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