Ruthenium-catalyzed selective addition of carboxylic acids to alkynes. A novel synthesis of enol esters

…, Y Hori, Y Yamakawa, Y Watanabe

Index: Mitsudo, Take-aki; Hori, Yoji; Yamakawa, Yasushi; Watanabe, Yoshihisa Journal of Organic Chemistry, 1987 , vol. 52, # 11 p. 2230 - 2239

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Citation Number: 137

Abstract

Carboxylic acids react with alkynes in the presence of a catalytic amount of bis (~ 5- cyclooctadienyl) ruthenium/trialkylphosphine/maleic anhydride in toluene at 60-80" C to give enol esters having a terminal methylene group in good to excellent yields with high regioselectivity. The deuterium distributions in the products of the reaction of acetic acid-d with 1-hexyne and ethyl propargyl carbonate were examined. Kinetic measurements ...