17349-87-0Relevant academic research and scientific papers
A new convenient synthesis of methyl 4-oxoalkanoates
Kulinkovich,Sorokin
, p. 361 - 362 (1994)
Methyl 4-oxoalkanoates have been obtained in good yields by treatment of 1,2-dichloro-2-alken-4-ones with sodium carbonate in methanol followed by acid-catalyzed hydrolysis of the intermediate 5-alkyl-2,2-dimethoxy-2,3-dihydrofurans.
Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters to synthesize γ-ketone esters
Lai, Luhao,Li, A-Ni,Zhou, Jiawei,Guo, Yarong,Lin, Li,Chen, Wei,Wang, Rui
, p. 2185 - 2190 (2017/03/17)
This work concerns the Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters with TMEDA as an additive. The isomerization proceeded under mild conditions and afforded γ-keto esters in high yield (up to 96%) within 2 h. Both (Z)- and (E)-γ-hydroxy-α,β-alkenoic esters were tolerated under the reaction conditions. This transformation involves the in situ formation of a dienolate intermediate from the easily accessible γ-hydroxy-α,β-alkenoic ester. The in situ generated dienolate can react with benzaldehyde and undergo a practical, useful tandem allylic isomerization-Aldol reaction to afford more functionalized compounds.
APPLICATIONS OF THE THERMAL ENE REACTION OF ALDEHYDE t-BUTYL- AND PHENYL- HYDRAZONES
Baldwin, Jack E.,Adlington, Robert M.,Jain, Ashok U.,Kolhe, Jayant N.,Perry, Matthew W. D.
, p. 4247 - 4252 (2007/10/02)
The Thermal Ene reaction of aldehyde t-butyl- and phenyl- hydrazones with enophiles gave C-trapped azo-adducts which can be diverted into synthetically useful γ-keto-esters, γ-keto-nitriles, γ-alkyl-2-pyrrolidones, and γ-amino-esters.
Michael Additions of Hydrazones for Carbon-Carbon Bond Formation
Baldwin, Jack E.,Adlington, Robert M.,Bottaro, Jeffrey C.,Jain, Ashok U.,Kolhe, Jayant N.,et al.
, p. 1095 - 1096 (2007/10/02)
The lithium salts of t-butyl- and trityl-hydrazones react with methyl crotonate to form C-trapped azo-esters and similar products were observed from a thermal ene-reaction of aldehyde t-butylhydrazones with methyl acrylate or acrylonitrile, and aldehyde phenylhydrazones with methyl acrylate; these products can be diverted into synthetically useful γ-keto-esters, γ-keto-nitriles, saturated esters, γ-alkyl-2-pyrrrolidones, and γ-amino-esters.
RUTHENIUM HYDRIDE-CATALYZED DOUBLE BOND MIGRATION OF 2,5-DIMETHOXY-2,5-DIHYDROFURANS. A NEW PROCESS FOR THE PREPARATION OF γ-KETOESTERS
Hirai, Kenji,Suzuki, Hiroharu,Kashiwagi, Hiroshi,Moro-Oka, Yoshihiko,Ikawa, Tsuneo
, p. 23 - 26 (2007/10/02)
γ-Ketoesters are obtained in excellent yields by means of double bond migration of 2,5-dimethoxy-2,5-dihydrofurans mediated by a ruthenium hydride complex, HRuCl(PPh3)3(C6H5CH3) or HRuCl(CO)(PPh3)3, and subsequent hydrolysis in acidic media.
