Three-Component and One-Pot Reaction between Aromatic Oximes and Dialkyl Acetylenedicarboxylates in the presence of Trimethyl Phosphite

Diastereoselective Synthesis of Functionalised Phosphonates by Three-Component reaction between Phosphites, Acetylene Diesters and Formanilides

“…The presence of phosphorus atom in the product is helpful for determining its relative configuration using the carbon-phosphorus coupling constants. In continuation of our previous work on the reaction between trialkyl phosphites and acetylene diesters in the presence of organic acidic compounds, [13][14][15][16] here we report the reaction between dialkyl acetylenedicarboxylates (DAADs), triethyl phosphite or triphenyl phosphite and formanilide derivatives to produce functionalised succinate phosphonates in good yields (Scheme 1).…”

“…For example, the reaction between trialkyl phosphites and dialkyl acetylenedicarboxylates (DAAD) in the presence of organic N-H, OH and C-H acidic compounds has been reported to produce phosphite ylides which may be isolated as stable compounds 9,10 or hydrolysed to phosphonate derivatives. [10][11][12][13][14][15][16] These phosphonates are usually formed in a stereoselective manner. The presence of phosphorus atom in the product is helpful for determining its relative configuration using the carbon-phosphorus coupling constants.…”

Three-Component Reaction between Trivalent Phosphorus Nucleophiles, Dialkyl Acetylenedicarboxylates and (2,4-Dinitrophenyl) Acetic Acid

“…7 The reaction of trimethyl phosphite with DMAD in the presence of 2-naphthol has been reported to afford stable 2,2-dimethoxy-3,4-dihydro-1-oxa-2-phosphaphenanthrene-3,4-dicarboxylates in good yield. 8 In continuation of our previous work on three-component reactions between trivalent phosphorus nucleophiles, acetylenic esters and organic acidic compounds, [9][10][11][12][13][14][15] we report here the results of our study on the reaction between acetylenic esters and phosphites or triphenylphosphine in the presence of (2,4-dinitrophenyl)acetic acid. * Correspondent.…”

Stereoselective Synthesis of Dialkyl 2-(Dialkoxyphosphoryl)-3-(3,5-Dioxo-4-Phenyl-[1,2,4]Triazolidin-1-yl) Succinates

“…Horner-Wadsworth-Emmons and related reactions), construction of the P-C bond remains a challenge. [4][5][6][7][8][9][10][11][12][13][14][15] In continuation of our work on the reaction between phosphites and acetylenic esters in the presence of organic NH-acids, [16][17][18][19][20] we wish to report the results of our study on the reaction between dialkyl acetylenedicarboxylates and Scheme 1 The reaction between dialkyl acetylenedicarboxylates and trialkyl(aryl) phosphites in the presence of 4-phenyl- [1,2,4]triazolidine-3,5-dione.…”