Recent advances in the synthesis of 5'-deoxynucleoside phosphonate analogs

: The present review focuses on the synthesis of cyclic 5-deoxynucleoside phosphonate analogs. The formation of various phosphonate alkyl moieties is accomplished through (i) Wittig (or HWE) type condensation to the nucleoside aldehyde moiety; (ii) nucleophilic displacement reaction using phosphonate anion or Lewis acid; (iii) Arbuzov reaction; (iv) olefin cross-metathesis between vinyl phosphonates and vinylated nucleosides; and (v) radical reaction and Pd catalyzed alkyne. For the coupling of nucleobases with cyclic moieties, the Mitsunobu reaction, and Sonogashira-type cross-coupling are usually applied. For the coupling of furanose moieties with nucleobases, Vorbrüggen-type condensation is generally applied. Addition reactions mediated by selenium ions are mainly applied for the coupling of carbocyclic moieties. Their biological activity results are summarized.

Enantioselective Michael Addition to Vinyl Phosphonates via Hydrogen Bond-Enhanced Halogen Bond Catalysis

An asymmetric Michael addition of malononitrile to vinyl phosphonates was accomplished by hydrogen bond-enhanced bifunctional halogen bond (XB) catalysis. 1H NMR titration experiments were used to demonstrate that halogen bonding,...

Synthesis and Characterization of Pd exchanged MMT Clay for Mizoroki-Heck Reaction

We successfully synthesized Pd@MMT clay using a cation exchange process. We characterized all the synthesized Pd@MMT clays using sophisticated analytical techniques before testing them as a heterogeneous catalyst for the Mizoroki - Heck reaction (mono and double). The highest yield of the Mizoroki-Heck reaction product was recovered using thermally stable and highly reactive Pd@ MMT-1 clay catalyst in the functionalized ionic liquid reaction medium. We successfully isolated 2-aryl-vinyl phosphonates (mono-Mizoroki-Heck reaction product) and 2,2-diaryl-vinylphosphonates (double-Mizoroki-Heck reaction product) using aryl halides and dialkyl vinyl phosphonates in higher yields. The low catalyst loading, easy recovery of reaction product and 8 times catalyst recycling are the major highlights of this proposed protocol.

Hydrophosphorylation of aliphatic alkynes catalyzed by CuNPs/ZnO for the synthesis of vinyl phosphonates. A DFT study on the reaction mechanism

A DFT study on the reaction mechanism for the synthesis of vinyl phosphonates catalyzed by CuNPs/ZnO. Essential role of the solvent and the catalyst support.

Base mediated 1,3-dipolar cycloaddition of α-substituted vinyl phosphonates with diazo compounds for synthesis of 3-pyrazolylphosphonates and 5-pyrazolcarboxylates

1-Substituted vinylphosphonates could serve as convenient precursors for functionalized pyrazoles in condition-controlled 1,3-dipolar cycloaddition reactions.