An efficient one-pot three-component procedure for the synthesis of new chiral spiro-oxindolopyrrolizidines with highly regio-, diastereo-, and enantioselective from 1,3-dipolar cycloaddition of azomethine ylides and optically pure active cinamoyl oxazolidinone are described. The process occurs at room temperature in aqueous ethanol as green solvent and in the absence of any bidentate chelating...

The rhodium(II)-catalyzed formation of 1,3-dipoles has played a major role in facilitating the use of the dipolar cycloaddition reaction in modern organic synthesis. This is apparent from the increasing number of applications of this chemistry for the construction of heterocyclic and natural product ring systems. This chapter initially focuses on those aspects of rhodium(II) catalysis that cont...

1-Sulfonyl-1,2,3-triazoles, which are readily available through copper-catalyzed azide-alkyne cycloaddition, are stable precursors to Rh–azavinyl carbenes, as well as carbene complexes of other metals. Among other transformations, these reactive intermediates can be used for the introduction of a nitrogen atom into various heterocycles that are important in both synthetic and medicinal chemistr...

Biohybrid amphiphiles have been prepared from terminal azide functionalised polystyrene and an alkyne functionalised peptide or protein via a Cu(I) catalysed Huisgen [3 + 2] dipolar cycloaddition reaction.

The copper catalyzed 1,3-dipolar cycloaddition of 4-butoxyphenylazide with 2-, 3- or 4-ethynylpyridine furnishes 1,4-diaryltriazoles, which display turn-on fluorescence upon addition of metal cations.

Copper-catalyzed, thermal or microwave promoted 1,3-dipolar cycloaddition (Click Reaction) of 2-propynyl and 3-butynyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-glycopyranosides in the D-gluco, D-galacto and D-manno series afford the corresponding dimeric cycloaddition products.

The synthesis and antibacterial activity of the title compounds having an isoxazolidine ring at the C-2 position are described. These derivatives were synthesized by the 1,3-dipolar cycloaddition reaction of nitrone with 2-vinyl carbapenems. This 1,3-dipolar cycloaddition reaction proceeded regioselectively to give diastereomeric isomers of 2(-isoxazolidin-5-yl)carbapenems. It was ascertained t...

Acid treatment of densely substituted 2-silyl-1,2-dihydropyridines provides a new and convenient entry to reactive azomethine ylides that can (1) be protonated and reduced with high stereoselectivity to give piperidines, (2) participate in [3 + 2] dipolar cycloaddition to give tropanes, and (3) undergo a Nazarov-like 6-π electrocyclization that upon reduction give 2-azabicyclo[3.1.0] systems.

Several regioselectively π-extended, pyrrole fused porphyrinoids have been synthesized by the 1,3-dipolar cycloaddition of meso-alkylidene-(benzi)porphyrins. Pd(II) complexes gave oxidation resistant, bis-pyrrole fused adducts. The repeated 1,3-dipolar cycloaddition followed by oxidation-reduction of pentaphyrin analogs afforded π-extended porphyrin analogs.