Catalytic Enantioselective Isocyanide‐Based Reactions: Beyond Passerini and Ugi Multicomponent Reactions

Abstract

The development of catalytic enantioselective isocyanide‐based reactions is currently of great interest because the resulting products are valuable in organic synthesis, pharmacological chemistry, and materials science. This review assembles and comprehensively summarizes the recent achievements in this rapidly growing area according to the reaction types. Special attention is paid to the advantages, limitations, possible mechanisms, and synthetic applications of each reaction. In addition, a personal outlook on the opportunities for further exploration is given at the end.

Supported l-tryptophan on Fe3O4@SiO2 as an efficient and magnetically separable catalyst for one-pot construction of spiro[indene-2,2′-naphthalene]-4′-carbonitrile derivatives

“…Multicomponent reactions (MCRs) and associated one-pot synthesis such as domino, tandem and cascade reactions have always been one of the most signicant scopes in the development of new methodologies in organic synthesis and catalysis due to their great applications, particularly in pharmaceutical studies. [1][2][3][4] MCRs oen produce highly complex molecules from simple precursors, thus, avoiding complicated purication steps and saving solvents, reagents and times. [5][6][7] Spiro compounds show a broad range of effective performance in pharmacology.…”

Diastereo‐ and Enantioselective Silver‐Catalyzed [3+3] Cycloaddition and Kinetic Resolution of Azomethine Imines with Activated Isocyanides

“…The key results of extensive optimization of the reaction conditions are summarized in Table 1. Initially, we tested the use of Dixon‐type phosphine ligands [5c] L1 and L2 in combination with Ag 2 CO 3 , which have been successfully applied in [3+2] cycloaddition reactions of activated isocyanides, [4f] for our reaction. Gratifyingly, the formation of the desired product 3 aa was observed, albeit with moderate stereoselectivity (entries 1 and 2).…”

Crosslinking Trends in Multicomponent Hydrogels for Biomedical Applications

“…The crosslinking and functionalization of CMC was performed using Ugi/Passerini MCRs. [94][95][96][97] It was observed that the formation of carboxamide-skeletons during the crosslinking of CMC, enhanced the bioavailability of CMC multicomponent hydrogels. The hydrogel developed, exhibited a controlled delivery of gentamicin and showed antibacterial activity towards S. aureus and E. coli.…”