27044-89-9Relevant academic research and scientific papers
A new method for enol lactone synthesis by a Michael addition/cyclization sequence
Itoh, Kennosuke,Kanemasa, Shuji
, p. 1799 - 1802 (2003)
Reactions of cyclic 1,3-dicarbonyl compounds with 1-(2-alkenoyl)-4-bromo-3,5-dimethylpyrazoles under the double catalytic activation conditions using both catalytic amounts of Lewis acid and amine catalysts provide a new direct synthetic route to enol lactones. Thus, 1,3-cyclohexanedione is allowed to react with 4-bromo-1-crotonoyl-3,5-dimethylpyrazole, in tetrahydrofuran at room temperature in the presence of both catalytic amounts (10 mol% each) of nickel(II) perchlorate hexahydrate and 2,2,6,6-tetramethylpiperidine, to give 4,7,7-trimethyl-3,4,5,6,7,8-hexahydrobenzopyran-2(H),5-dione in a good yield. This reaction does not proceed or is too slow under the reaction conditions other than the double catalytic activation conditions.
A highly efficient CuI nanoparticles-catalyzed synthesis of tetrahydrochromenediones and dihydropyrano[c]chromenediones under grinding
Abdolmohammadi, Shahrzad,Ghiasi, Reza,Ahmadzadeh-Vatani, Sam
, p. 777 - 782 (2016/07/27)
A concise and CuI nanoparticle-catalyzed synthesis of tetrahydrochromenediones and dihydropyrano[c]chromenediones under solvent-free grinding conditions via the three-component condensation reaction of Meldrum's acid, an aromatic aldehyde, and an active m
Enantioselective synthesis of enol lactones from tandem Michael addition/lactonization catalyzed by a chiral squaramide catalyst
Zhao, Bo-Liang,Du, Da-Ming
, p. 310 - 317 (2014/04/03)
The enantioselective tandem Michael addition reaction of dimedone and related 1,3-dicarbonyl compounds with α,β-unsaturated N-acylated succinimides catalyzed by a chiral squaramide catalyst has been investigated. This reaction provides a new approach for the synthesis of chiral enol lactones in good yields with moderate to high enantioselectivities (up to 88% ee) through the enantioselective Michael addition followed by lactonization and removal of the succinimide auxiliary.
Concise formal synthesis of (-)-7-deoxyloganin via N-heterocyclic carbene catalysed rearrangement of α,β-unsaturated enol esters
Candish, Lisa,Lupton, David W.
experimental part, p. 8182 - 8189 (2012/01/04)
NHC catalysed rearrangement of α,β-unsaturated enol esters derived from formyl acetates and cyclopentyl annulated α,β- unsaturated acids provides the cyclopentapyranone core of (-)-7-deoxyloganin (1) with diastereo- and chemoselectivity in 6 steps startin
N-heterocyclic carbene-catalyzed generation of α,β-unsaturated acyl imidazoliums: Synthesis of dihydropyranones by their reaction with enolates
Ryan, Sarah J.,Candish, Lisa,Lupton, David W.
supporting information; experimental part, p. 14176 - 14177 (2010/02/16)
(Chemical Equation Presented) Catalytic generation of α,β- unsaturated acyl imidazolium cations and enolates has been achieved, and their involvement in a Michael addition acylation sequence exploited, to provide a range of dihydropyranones. α,β-Unsaturat
