Platinum-catalyzed intramolecular hydroalkoxylation of gamma- and delta-hydroxy olefins to form cyclic ethers.

Journal Article (Journal Article)

Reaction of 2,2-diphenyl-4-penten-1-ol with a catalytic mixture of [PtCl2(H2C=CH2)]2 (1 mol %) and P(4-C6H4CF3)3 (2 mol %) at 70 degrees C for 24 h led to the isolation of 2-methyl-4,4-diphenyltetrahydrofuran in 78% yield. The platinum-catalyzed hydroalkoxylation of gamma-hydroxy olefins tolerated substitution at the alpha, beta, and gamma-carbon atoms and at the internal and cis and trans terminal olefinic positions. Platinum-catalyzed hydroalkoxylation tolerated a number of functional groups including pivaloate and acetate esters, amides, silyl and benzyl ethers, and pendant hydroxyl and olefinic groups. Pt-catalyzed olefin hydroalkylation was also applicable to the formation of fused- and spirobicyclic ethers and was effective for the hydroalkoxylation of delta-hydroxy olefins to form tetrahydropyran derivatives.

Full Text

Duke Authors

Cited Authors

  • Qian, H; Han, X; Widenhoefer, RA

Published Date

  • August 2004

Published In

Volume / Issue

  • 126 / 31

Start / End Page

  • 9536 - 9537

PubMed ID

  • 15291546

Electronic International Standard Serial Number (EISSN)

  • 1520-5126

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja0477773


  • eng