Rearrangement of propargylic esters: Metal-based stereospecific synthesis of (E)-and (Z)-Knoevenagel derivatives

…, L Riesgo, R Vicente, LA López, M Tomás

Index: Barluenga, Jose; Riesgo, Lorena; Vicente, Ruben; Lopez, Luis A.; Tomas, Miguel Journal of the American Chemical Society, 2007 , vol. 129, # 25 p. 7772 - 7773

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Citation Number: 63

Abstract

Alkoxy-substituted propargylic esters undergo regioselective 1, 3-acyloxy migration in the presence of Pt (II) and Cu (I) catalysts, allowing the preparation of α-ylidene-β-keto and- malonate esters. The reaction proved to also be stereodivergent as the Pt (II) and the Cu (I) catalysts perform the isomerization with complementary Z/E selectivity. Moreover, alkynyl- conjugated Knoevenagel products are produced from (bisalkynyl) methyl acetates. In such ...