Synthesis of Pyrrolidine C-Nucleosides via Heck Reaction

Abstract

[figure: see text] A novel method for the synthesis of pyrrolidine C-nucleosides has been developed. The key step of the synthesis is the palladium(0)-mediated coupling of a disubstituted N-protected 2-pyrroline and 5-iodouracil. C-Nucleoside 14 and its N-methyl derivative 15 can easily be converted to the corresponding phosphoramidite building blocks for DNA synthesis.

Efficient C--C cross-coupling reactions by (isatin)-Schiff base functionalized magnetic nanoparticle-supported Cu(II) acetate as a magnetically recoverable catalyst

“…2 Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions are the most widely used methods for extensive production of key intermediates during preparation of natural, 3 nonnatural, 4 and bioactive compounds. 5,6 Although homogeneous palladium complexes as conventional catalysts in crosscoupling reactions have shown high reaction rates, suitable turnover numbers, and sometimes perfect selectivity and yield, these types of catalysts suffer from the problem of recycling of the catalyst as well as instability during reaction at high temperatures. 7,8 Recoverability and reusability of the catalyst are a challenge from environmental and economic points of view, especially when precious metal catalysts are used.…”

Heterogeneously catalyzed phosphine-free heck cross-coupling reaction of aryl halides with reusable palladium(II) schiff base complex

“…[1][2][3] The use of such catalytic procedures has found applications in the preparation of many natural products, as well as in materials science and the agrochemical industry. [4][5][6][7] With various metals being employed in coupling reactions, palladium probably is the most frequently chosen transition metal due to its excellent catalytic efficiency in this type of reactions. [8][9][10][11][12] The palladium catalyzed Heck cross-coupling reaction of aryl halides with terminal alkenes, which provides a powerful tool for the formation of aryl-alkenes, [13][14][15] has been widely applied to such diverse areas as natural product syntheses and material sciences.…”

Palladium nanoparticles supported on layered hydroxide salts and their use in carbon-carbon coupling organic reactions

“…[20][21][22][23] It is well known that nanometric arrays confer a high catalytic efficiency to the materials because of their high surface:volume ratios. Several reports have demonstrated the potential of nanometric palladium particles in carboncarbon coupling reactions, 15,[22][23][24] which are important useful procedures for the synthetic organic chemistry, 25,26 with their products becoming key intermediates for the preparation of other organic materials, [27][28][29] natural products 30 and bioactive compounds, 31,32 such as taxol (antitumor agent) or cinnamic acid derivatives. 33 These products exhibit antibacterial or antifungal activities and some other are useful as ingredients for fragrances.…”