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An Atom-Economic and Selective Ruthenium-Catalyzed Redox Isomerization of Propargylic Alcohols. An Efficient Strategy for the Synthesis of Leukotrienes

Barry M. Trost and Robert C. Livingston

*Department of Chemistry, Stanford University, Stanford, California 94305-5080, Email: bmtroststanford.edu

B. M. Trost, R. C. Livinston, J. Am. Chem. Soc., 2008, 130, 11852-11853.

DOI: 10.1021/ja804105m (free Supporting Information)


Abstract

Readily available indenylbis(triphenylphosphine)ruthenium chloride in conjunction with an indium cocatalyst and Brønsted acid isomerizes primary and secondary propargylic alcohols in good yields to provide trans enals and enones exclusively. The presence of indium triflate and camphorsulfonic acid gives the best turnover numbers and reactivity with the broadest range of substrates.

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Key Words

Enones


ID: J48-Y2008-2400