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Regio- and stereoselective synthesis of alkyl allylic ethers via gold(I)-catalyzed intermolecular hydroalkoxylation of allenes with alcohols.

Publication ,  Journal Article
Zhang, Z; Widenhoefer, RA
Published in: Organic letters
May 2008

Reaction of 1-phenyl-1,2-butadiene with 2-phenyl-1-ethanol catalyzed by a 1:1 mixture of a gold(I) N-heterocyclic carbene complex and AgOTf at room temperature for 1 h led to isolation of (E)-(3-phenethoxy-1-butenyl)benzene in 96% yield as a single regio- and stereoisomer. Gold(I)-catalyzed intermolecular allene hydroalkoxylation was effective for monosubsituted, 1,1- and 1,3-disubstituted, trisubstituted, and tetrasubstituted allenes and for a range of primary and secondary alcohols, methanol, phenol, and propionic acid.

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Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

May 2008

Volume

10

Issue

10

Start / End Page

2079 / 2081

Related Subject Headings

  • Stereoisomerism
  • Silver
  • Organometallic Compounds
  • Organic Chemistry
  • Molecular Structure
  • Hydroxylation
  • Gold
  • Ethers
  • Catalysis
  • Alkylation
 

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Zhang, Z., & Widenhoefer, R. A. (2008). Regio- and stereoselective synthesis of alkyl allylic ethers via gold(I)-catalyzed intermolecular hydroalkoxylation of allenes with alcohols. Organic Letters, 10(10), 2079–2081. https://doi.org/10.1021/ol800646h
Zhang, Zhibin, and Ross A. Widenhoefer. “Regio- and stereoselective synthesis of alkyl allylic ethers via gold(I)-catalyzed intermolecular hydroalkoxylation of allenes with alcohols.Organic Letters 10, no. 10 (May 2008): 2079–81. https://doi.org/10.1021/ol800646h.
Zhang, Zhibin, and Ross A. Widenhoefer. “Regio- and stereoselective synthesis of alkyl allylic ethers via gold(I)-catalyzed intermolecular hydroalkoxylation of allenes with alcohols.Organic Letters, vol. 10, no. 10, May 2008, pp. 2079–81. Epmc, doi:10.1021/ol800646h.
Journal cover image

Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

May 2008

Volume

10

Issue

10

Start / End Page

2079 / 2081

Related Subject Headings

  • Stereoisomerism
  • Silver
  • Organometallic Compounds
  • Organic Chemistry
  • Molecular Structure
  • Hydroxylation
  • Gold
  • Ethers
  • Catalysis
  • Alkylation