15174-78-4Relevant articles and documents
Palladium-Catalyzed Cascade Carbonylation to α,β-Unsaturated Piperidones via Selective Cleavage of Carbon–Carbon Triple Bonds
Beller, Matthias,Ge, Yao,Jackstell, Ralf,Jiao, Haijun,Spannenberg, Anke,Yang, Ji,Ye, Fei
supporting information, p. 22393 - 22400 (2021/09/08)
A direct and selective synthesis of α,β-unsaturated piperidones by a new palladium-catalyzed cascade carbonylation is described. In the presented protocol, easily available propargylic alcohols react with aliphatic amines to provide a broad variety of interesting heterocycles. Key to the success of this transformation is a remarkable catalytic cleavage of the present carbon–carbon triple bond by using a specific catalyst with 2-diphenylphosphinopyridine as ligand and appropriate reaction conditions. Mechanistic studies and control experiments revealed branched unsaturated acid 11 as crucial intermediate.
Michael Reaction of Conjugated Nitro Olefins with Carboxylic Acid Dianions and with Ester Enolates: New Synthesis of γ-Keto Acids and γ-Keto Esters
Miyashita, Masaaki,Yamaguchi, Ryuji,Yoshikoshi, Akira
, p. 2857 - 2863 (2007/10/02)
Base-sensitive conjugated nitro olefins 2 reacted with lithium dianions of carboxylic acids 3 or with lithium enolates of esters 4 at a low temperature of ca. -100 deg C, and subsequent treatment of the Michael adducts with aqueous acid yielded γ-keto acids 5 or esters 5' in a one-pot operation, respectively.Results of both the reactions have been compared.Some applications of the resulting γ-keto esters in organic synthesis have also been demonstrated in lactone synthesis and cyclenone annulation.
