Azlactones participate in stereoselective reactions with electron-deficient alkenes and N-sulfonyl aldimines to give products of 1,3-dipolar cycloaddition and Mannich addition reactions, respectively. Both of these reactions proceed with good to excellent diastereo- and enantioselectivity using a single class of gold catalysts, namely C(2)-symmetric bis(phosphinegold(I) carboxylate) complexes. ...

The 1,3-dipolar cycloaddition of acyclic 2-diazo-1,3-dicarbonyl compounds (DDC) and thioketones preferably occurs with Z,E-conformers and leads to the formation of transient thiocarbonyl ylides in two stages. The thermodynamically favorable further transformation of C=S ylides bearing at least one acyl group is identified as the 1,5-electrocyclization into 1,3-oxathioles. However, in the case o...

The synthesis of the (2S)-[3-(anthracen-9-yl)-4,5-dihydroisoxazol-5-yl]methyl 2-[(tert-butoxycarbonyl)amino]propanoate is obtained through the 1,3-dipolar cycloaddition of the stable anthracenenitrile oxide and the N-Boc protected (S)-alanine allyl ester as dipolarophile. The structure and the fluorescence properties are described upon the relative analytical and spectroscopic data.

A novel and highly stereoselective synthesis of Z-β-enaminonitriles from azides and α,β-unsaturated nitriles is reported. The reaction proceeds via a 1,3-dipolar cycloaddition-ring cleavage-rearrangement cascade mediated by a catalytic amount of Sc(OTf)3. A plausible reaction mechanism for this process is depicted.

A dynamic azomethine ylide system was established using Sc(OTf)3 and Ag/Taniaphos as catalysts. The system was subsequently kinetically resolved in a tandem 1,3-dipolar cycloaddition process where the silver complex acted as both a reaction catalyst and an external selector, resulting in the formation of an exclusive pyrrolidine product in good yield and enantiopurity.

The catalytic asymmetric three-component 1,3-dipolar cycloaddition of 3-amino oxindoles with aldehydes and nitroolefins under the catalysis of a chiral phosphoric acid is reported. The reaction provides a facile approach to synthesize a diverse array of spiro[pyrrolidine-2,3'-oxindoles] in high yields with excellent diastereo- and enantioselectivities under mild conditions.

Diastereoselective reactions between 4-formylpyrazoles, N-substituted maleimides and glycine derivates led to new series of pyrazolyldipyrrolo [3,4-a:3',4'-f]pyrrolizines and pyrazolylpyrrolo[3,4-c]pyrroles in good yields. The reactions proceeded by a domino process through azomethine ylides formed in situ via a 1,3-dipolar cycloaddition reaction.

Isosorbide was esterified with acryloyl chloride and crotonic acid yielding isosorbide diacrylate (9a) and isosorbide dicrotonate (9b), which were reacted with benzaldehyde oxime in the presence of zinc(II) iodide and boron triflouride etherate as catalysts to obtain N-alkylated dinitrones 10a/b. Poly(isosorbide itaconite -co- succinate) 13 as a bio-based unsaturated polyester was cross-linked ...

Multivalent dendrimeric peptides were synthesized via a microwave-assisted Huisgen 1,3-dipolar cycloaddition between azido peptides and dendrimeric alkynes in yields ranging from 46 to 96%.

Abstract An efficient organo-photocatalytic method for the synthesis of tetrasubstituted pyrroles bearing a ketone, ester, alcohol, or nitro group at 3-position has been developed. The reaction involves visible-light-mediated formal [3+2] dipolar cycloaddition between 2H-azirines and α-substituted nitroalkenes followed by denitration debromination sequence. notable features protocol are excelle...