Platinum-Catalyzed Intramolecular Hydroalkoxylation of γ- and δ-Hydroxy Olefins to Form Cyclic Ethers

Hua Qian, Xiaoqing Han, and Ross A. Widenhoefer*
P. M. Gross Chemical Laboratory, Duke University, Durham, North Carolina 27708-0346
J. Am. Chem. Soc., 2004, 126 (31), pp 9536–9537
DOI: 10.1021/ja0477773
Publication Date (Web): July 16, 2004
Copyright © 2004 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, rwidenho@chem.duke.edu

Abstract

Abstract Image

Reaction of 2,2-diphenyl-4-penten-1-ol with a catalytic mixture of [PtCl2(H2CCH2)]2 (1 mol %) and P(4-C6H4CF3)3 (2 mol %) at 70 °C for 24 h led to the isolation of 2-methyl-4,4-diphenyltetrahydrofuran in 78% yield. The platinum-catalyzed hydroalkoxylation of γ-hydroxy olefins tolerated substitution at the α, β, and γ-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 δ-hydroxy olefins to form tetrahydropyran derivatives.

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History

  • Published In Issue August 11, 2004
  • Received April 17, 2004

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