Ruthenium Catalyzed Synthesis of Butenolides and Pentenolides via Contra-Electronic. alpha.-Alkylation of Hydroxyalkynoates

BM Trost, TJJ Mueller, J Martinez

Index: Trost, Barry M.; Mueller, Thomas J. J.; Martinez, Jose Journal of the American Chemical Society, 1995 , vol. 117, # 7 p. 1888 - 1899

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Citation Number: 102

Abstract

Abstract: The addition of alkenes to 4-hydroxy-2-alkynoates in an Alder-ene-type mode produces butenolides in the presence of a ruthenium catalyst. Among various ruthenium complexes, CpRu (C0D) Cl appears to be most effective. The best results occur in aqueous DMF or methanol, with the latter preferred. The reaction proceeds with excellent chemoselectivity. Even nonreacting double bonds do not isomerize. The regioselectivity ...

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