Construction of Enantiopure Pyrrolidine Ring System via Asymmetric [3+2]-Cycloaddition of Azomethine Ylides

Synthesis of MeO-PEG-Supported Ferrocenyloxazoline Ligands and Their Application in Asymmetric Catalysis

“…The [3＋2] cycloaddition reaction of azomethine ylide with olefinic dipolarophiles constitutes a straightforward approach to the synthesis of highly substituted chiral pyrrolidine derivatives. [34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49][50] So far, many laboratories have reported the catalytic asymmetric [3＋2] cycloadditions with azomethine ylides by means of a variety of ligand-metal combinations. Our group reported that the ferrocenyloxazoline derived chiral N,P ligand showed excellent performance in the Ag(I)-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides.…”

Ultrasound-assisted, ZnBr2-catalyzed regio- and stereoselective synthesis of novel 3,3′-dispiropyrrolidine bisoxindole derivatives via 1,3-dipolar cycloaddition reaction of an azomethine ylide

“…[1][2][3] In recent years the azomethine ylide has gained a vital place in the synthesis of heterocyclic compounds as it serves as an important building block for the construction of nitrogen-containing five membered heterocycles, [4][5][6][7][8] which are often an integral part of many natural products and bioactive molecules. 9,10 The 3,3′-spirocyclooxindole skeleton is found in a growing number of natural or synthetic products presenting various biological activities.…”

1,3-Dipolar cycloaddition reactions of azomethine ylides with aromatic dipolarophiles

“…Azomethine ylides, which contain four electrons distributed over the π orbitals of a C-N-C group, are examples of bent allyl anion-type 1,3-dipoles. 41 The ylides can be classified as non-stabilized (where R 1 , R 2 and R 3 = H or alkyl) or stabilized either by electron-withdrawing/electron-donating groups at the appropriate termini of the ylide or by N-metalation. 41 Azomethine ylides are mostly generated in situ due to their high reactivity and/or transient existence; however, in some cases, stabilized azomethine ylides have been isolated.…”

“…41 The ylides can be classified as non-stabilized (where R 1 , R 2 and R 3 = H or alkyl) or stabilized either by electron-withdrawing/electron-donating groups at the appropriate termini of the ylide or by N-metalation. 41 Azomethine ylides are mostly generated in situ due to their high reactivity and/or transient existence; however, in some cases, stabilized azomethine ylides have been isolated. [42][43][44] The isoindole framework is found within a large range of natural products and frequently features in bioactive natural products, synthetic agrochemicals, pharmaceuticals and dyes.…”