Catalytic One-Pot Double Asymmetric Cascade Reaction: Synthesis of Chlorinated Oxindoles and Geminal Diamines

Abstract

A multicomponent catalytic double asymmetric cascade reaction for obtaining chlorinated oxindoles and C−N aminals simultaneously is described. A calcium VAPOL phosphate complex was shown to catalyze two enantiocontrolled multicomponent reactions utilizing 3-aryloxindoles, N-Boc imines, and N-chlorophthalimide, which afforded two structurally complex and diverse chiral products with high levels of stereocontrol in one pot. This transformation is facile and has a high degree of both step and atom economy.

Catalytic Strategies for the Asymmetric Construction of Cyclic Frameworks with a Halogenated Tetrasubstituted Stereocenter

“…This DACR proceeded mild reaction conditions with low catalyst loading, and tolerated a wide range of substrates. The chlorinated products could be obtained with excellent yields and enantioselectivities (Scheme ) …”

Zirconium@guanine@MCM‐41 nanoparticles: An efficient heterogeneous mesoporous nanocatalyst for one‐pot, multi‐component tandem Knoevenagel condensation–Michael addition–cyclization Reactions

“…[10,11] These reactions have become a strong synthetic methodology for the rapid preparation of small-molecule libraries that reduce the number of synthetic steps and can be obtained in one pot with much fewer steps. [8,[12][13][14] The major advantages of multicomponent reactions are one-pot synthesis, high atom economy and time-saving without isolation of intermediates or generating byproducts. [14][15][16][17][18][19] In particular, Phenazines and chromenes have attracted increasing attention in drug discovery and medicinal chemistry which can be synthesized by a one-pot two-steps procedure.…”

“…[8,[12][13][14] The major advantages of multicomponent reactions are one-pot synthesis, high atom economy and time-saving without isolation of intermediates or generating byproducts. [14][15][16][17][18][19] In particular, Phenazines and chromenes have attracted increasing attention in drug discovery and medicinal chemistry which can be synthesized by a one-pot two-steps procedure. [8,[18][19][20] These compounds have been reported as biological active species which involve anticancer, antifungal, antiplasmodial, antimalarial, antibacterial, cancer chemopreventive, antiparasitic and antichagasagen activities.…”

“…[8,[18][19][20] These compounds have been reported as biological active species which involve anticancer, antifungal, antiplasmodial, antimalarial, antibacterial, cancer chemopreventive, antiparasitic and antichagasagen activities. [19] Among the wide range of N-containing heterocyclic compounds, the pyrazolones and bispyrazolones were paid much attention for their various biological activities, such as antitumor, [21] antiinflammatory, [22] antifilarial agents, [23] dyes, [24] pesticides, [14] selective COX-2 inhibitory, [25] antibacterial [23] and fungicides. [15] Moreover, these compounds were used as extracting agents for some metal ions in analytical chemistry [26] and ligands in coordination chemistry.…”

Enantioselective Peroxidation of C-alkynyl imines enabled by chiral BINOL calcium phosphate

“…On the other hand, chiral alkali and alkaline earth metal phosphates have proven to be versatile and efficient bifunctional catalysts in many asymmetric transformations. 12 However, to the best of our knowledge, only one report by Shao and co-workers has presented the asymmetric aza-Mannich-type reaction of C -alkynyl N -Boc N , O -acetals promoted by lithium phosphate 11 d . Therefore, direct catalytic asymmetric functionalization of C -alkynyl N -Boc N , O -acetals catalyzed by chiral alkali and alkaline earth metal phosphates, especially calcium phosphate, has remained elusive.…”