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

Journal Article (Journal Article)

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.

Full Text

Duke Authors

Cited Authors

  • Zhang, Z; Widenhoefer, RA

Published Date

  • May 2008

Published In

Volume / Issue

  • 10 / 10

Start / End Page

  • 2079 - 2081

PubMed ID

  • 18412355

Electronic International Standard Serial Number (EISSN)

  • 1523-7052

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol800646h


  • eng