Synthesis of dimethyl-1-(trifluoromethyl)-3H-pyrrolizine-2,3-dicarboxylate using phosphorus compounds

Abstract

A general and practical route for the synthesis of phosphorus compounds containing trifluoromethyl or trichloromethyl groups by a one-pot condensation triphenylphosphine and dialkyl acetylenedicarboxylate in the presence of an NH-acid such as 2,2,2-trifluoro-1-(1H-pyrrol-2-yl)ethanone or 2,2,2-trichloro-1-(1H-pyrrol-2-yl)ethanone is described. The product obtained from the fluorinated compound undergoes an intramolecular Wittig reaction in boiling THF. This method offers a simple procedure for the preparation of dimethyl 1-(trifluoromethyl)-3H-pyrrolizine-2, 3-dicarboxylate.

Stable phosphorus ylides and heterocyclic phosphonate esters derivatives synthesised from stereoselective reactions between triphenyl phosphite and activated acetylenic esters

“…Phosphorus ylides are important reactants in organic chemistry because of their applications in the synthesis of organic products, [1][2][3][4][5][6] especially naturally occurring products with biological and pharmacological activity. [7][8][9][10][11][12][13][14][15][16][17][18][19] Recently, organic reactions in water have attracted much attention because water is the most readily available safe solvent. [20][21][22][23] The use of water as a solvent has been uncommon in organic reactions for several reasons, among them the insolubility of the reactant, the incompatibility of intermediates with water and the competition of the desired reaction with hydrolysis.…”

Phenanthridine or Isoquinoline are Good Reagents for the Synthesis of Enamino Esters

“…An efficient synthesis of a new class of enamino esters from reaction between phenanthridine 1 or isoquinoline 5 and activated acetylenic esters 2 or 6 as a Michael acceptor [27][28][29][30][31][32][33][34] was undertaken in the presence of heterocyclic NH compounds (succinimide, 5-nitroindazole, benzoxazole, 6-chlorobenzoxazole, carbazole and 3,6-dibromocarbazole) or 1,3-dicarbonyl compounds such as 1,3-dimethylbarbituric acid and 1,3diethyl-2-thiobarbituric acid at ambient temperature. Reactions were carried out by first mixing the phenanthridine or isoquinoline and heterocyclic NH or 1,3-dicarbonyl compounds and then the acetylenic ester was added slowly.…”

Water–acetone Media Enforced Chemoselective Synthesis of 2-substituted Pyrrole Stable Phosphorus Ylides from Reaction between Pyrrole and Acetylenic Esters in the Presence of Triphenylphosphine

“…[2][3][4][5][6][7][8][9][10][11][12][13] There are many systematic investigations on the synthesis of the reactions between trivalent phosphorus nucleophiles and α,β-unsaturated carbonyl compounds in the presence of a proton source such as alcohols or CH-acids. 2,[13][14][15][16][17][18][19][20][21][22][23][24]…”