944940-75-4Relevant academic research and scientific papers
Rearrangement of propargylic esters: Metal-based stereospecific synthesis of (E)- and (Z)-knoevenagel derivatives
Barluenga, Jose,Riesgo, Lorena,Vicente, Ruben,Lopez, Luis A.,Tomas, Miguel
, p. 7772 - 7773 (2007)
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 a case, the reaction is chemoselective as the 1,3-acetyl migration takes place through the alkoxyalkyne group in preference over the phenylalkyne group. The resulting (E)-alkynylenone unit suffers metal-catalyzed cyclization into the furyl ring, generating a copper(I) carbene species. Copyright
Efficient organocatalyzed solvent-free selective synthesis of conjugated enones
Goswami, Papori,Das, Babulal
scheme or table, p. 897 - 900 (2009/05/27)
A series of conjugated dienones and enones were synthesized by a reaction of both conjugated and simple aldehydes, respectively, with 1,3-dicarbonyl compounds and aldehydes under solvent-free conditions at room temperature in the presence of 10 mol % of l-proline as catalyst. The selective formation of one isomer was observed exclusively with most of the 1,3-dicarbonyl compounds and aldehydes. The most commonly formed xanthene derivative from the cyclic diketones is inhibited with our protocol, with the exclusive formation of conjugated dienones only.
