A rapid and divergent access to chiral azacyclic nucleoside analogues has been established via highly exo-selective and enantioselective 1,3-dipolar cycloaddition of azomethine ylides with β-nucleobase substituted acrylates. Using 1 mol% of a chiral copper complex, various chiral azacyclic nucleoside analogues were obtained in high yields, excellent exo-selectivities and enantioselectivities (9...

Herein we describe the synthesis of the first Thalidomide-biotin analogue in order to initiate investigations into the unknown molecular mode of action of Thalidomide. In this manner we describe the attachment of biotin tether through the Huisgen 1,3-dipolar cycloaddition or "click" synthetic methodology.

The regioselective intramolecular 1,3-dipolar cycloaddition of the phenylsulfonylallene-nitrone derivatives has been developed. This reaction showed that the distal double bond of the allene exclusively reacted with the nitrone group to produce the bicyclic isoxazolidine derivatives regardless of the substitution pattern on the allenyl moiety.

A complete stereocontrol of 1,3-dipolar cycloaddition of N-metalated azomethine ylides onto endohedral fullerene H2@C60 is reported for the first time. The stereodivergent synthesis of either the cis or the trans endohedral cycloadduct is achieved with excellent diastereo- and enantioselectivities.

A short and modular synthetic pathway using intramolecular 1,3-dipolar cycloaddition reactions and yielding functionalized isoxazoles, isoxazolines, and isoxazolidines is described. The change in shape of previous compounds and those in this study is quantified and compared using principal moment-of-inertia shape analysis.

Some 5-(1,2,3-triazol-1-ylmethyl)uridine derivatives were synthesized via the 1,3-dipolar cycloaddition of a 5-azidomethyluridine derivative with substituted acetylenes. The antiviral activities of these compounds against hepatitis A virus (HAV, MBB cell culture-adapted strain) and Herpes simplex virus type-1 (HSV-1) were tested.

The explosively-growing applications of the Cu-catalyzed Huisgen 1,3-dipolar cycloaddition reaction between organic azides and alkynes (CuAAC) have stimulated an impressive number of reports, in the last years, focusing on recoverable variants of the homogeneous or quasi-homogeneous catalysts. Recent advances in the field are reviewed, with particular emphasis on systems immobilized onto polyme...

An unprecedented functionalization of multi-walled carbon nanotubes (MWCNTs) has been conveniently achieved by the 1,3-dipolar cycloaddition of a cyclic nitrone. This organic functionalization yields materials with a great solubility in DMF (close to 10 mg per mL of DMF) preferentially occurring at the defects of the MWCNT sp(2) network.

We report the first use of a photoinduced 1,3-dipolar cycloaddition reaction in "stapling" peptide sidechains to reinforce a model peptide helical structure with moderate to excellent yields; the resulting pyrazoline "staplers" exhibit unique fluorescence useful in a cell permeability study.

The one-pot synthesis of multisubstituted pyrazole derivatives was achieved via catalyst-free 1,3-dipolar cycloaddition of ethyl diazoacetate and nitroalkenes as the key step and elimination of the leaving group (NO(2) or Br) followed by intramolecular proton transfer with satisfactory yields.