Hydroxyl-group-activated azomethine ylides in organocatalytic H-bond-assisted 1,3-dipolar cycloadditions and beyond

Abstract

1,3-Dipolar cycloaddition constitutes powerful means for the synthesis of five-membered heterocycles. Recently, the potential of this field of chemistry has been expanded by the employment of organocatalytic activation strategies. One...

Catalytic Asymmetric Dearomative 1,3-Dipolar Cycloaddition of 2-Nitrobenzothiophenes and Isatin-Derived Azomethine Ylides

“…Catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides with alkenes has proven to be a straightforward approach to enantioenriched pyrrolidine-containing compounds with structural diversity . In this research area, the reactions with electron-deficient nitroalkenes as dipolarophiles have been widely realized by transition-metal catalysis and organocatalysis .…”

Intramolecular Hydrogen-Bond Activation: Strategies, Benefits, and Influence in Catalysis

“…We hope this Perspective can complement some specific works already published in the literature focused on azomethine ylide derivatives, 13 providing a general outline on this intramolecular H-bond interaction for the activation of multiple substrates in metal and organocatalytic areas. To do so, different examples from the last 15 years have been reviewed, focusing on functional group types that have been boosted as electrophiles and nucleophiles.…”

Construction of heterocyclic rings from cyclopropenes

“…25 The interesting pharmacological effects of natural products with the 3-spiropyrrolidine oxindole framework have attracted much attention from synthetic chemists. 26 As a typical example, 1,3-dipolar cycloaddition reaction of azomethine ylides derived from isatins and α-amino acids has been well studied. For instance, one-pot three-component reactions between cyclopropenes 103, α-amino acids 104, and substituted isatins 105 have been established, which enable a direct synthesis of 3-spiro[cyclopropa[a]pyrrolizine]oxindoles 106 in moderate to high yields (Scheme 17a).…”

“…25 The interesting pharmacological effects of natural products with the 3-spiropyrrolidine oxindole framework have attracted much attention from synthetic chemists. 26…”