84796-94-1Relevant academic research and scientific papers
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.
MICHAEL REACTION OF SILYL ENOL ETHERS OR KETENE SILYL ACETALS WITH CONJUGATED NITRO OLEFINS ACTIVATED BY THE LEWIS ACID: NEW SYNTHESIS OF 1,4-DIKETONES AND gamma -KETO ESTERS.
Miyashita,Yanami,Kumazawa,Yoshikoshi
, p. 2149 - 2156 (2007/10/02)
New one-pot procedures for the synthesis of 1,4-diketones and gamma -keto esters utilizing conjugated nitro olefins are described. Reaction of silyl enol ethers with aliphatic nitro olefins in the presence of a Lewis acid affords 1,4-diketones in good yie
NEW SYNTHESIS OF Γ-KETO ACIDS FROM NITROOLEFINS AND CARBOXYLIC ACID DIANIONS
Miyashita, Masaaki,Yamaguchi, Ryuji,Yoshikoshi, Akira
, p. 1505 - 1508 (2007/10/02)
As a convenient synthetic method of γ-keto acids, oxoalkylation of carboxylic acids with nitroolefins was examinated.Carboxylic acid dianions reacted with conjugated nitroolefins at low temperature (-100 deg C) and a variety of γ-keto acids were obtained on acidic workup in moderate to good yields.
