Sequential and direct multicomponent reaction (MCR)-based dearomatization strategies

Abstract

This review focuses on the comprehensive understanding of the different multicomponent reaction (MCR) cascades involving dearomatization as the characteristic step.

The evaluation of chemoselectivity in multicomponent domino Knoevenagel/Diels-Alder reaction: A DFT study

“…6 By the way, the development of domino and other multicomponent reaction methodologies can provide convenient admission to produce more complex compounds from simple starting materials. 2,7,8 The incorporation of a Diels-Alder reaction sequence is the fundamental key to many interesting variants of these reactions. [9][10][11] In recent times, organocatalysis has emerged as a promising synthetic tool for constructing C-C and C-N bonds in aldol, 12 Michael, 13 Mannich, 14 Diels-Alder 15 and other reactions 16 with very good chemoelectivity and stereoselectivity.…”

“…MCRS make an easily achieved substituent diversity into the core structure by varying each component. 1,2 The improvement of reaction efficiency, the avoidance of toxic reagents, the reduction of waste, and the responsible utilization of our resources are critical concerns in modern synthetic organic chemistry. 3 Consisting of several bondforming reactions, the domino or tandem reactions address many of these…”

A Synthesis of Spirooxindole‐Isoindolinones Through Ugi Reaction Followed by Copper‐Catalyzed Tandem C−N/C−C Coupling Process

“…Over the past few decades, multicomponent reactions (MCRs) have extensively been employed as highly efficient synthetic strategies for the access of multifunctional molecular architectures under mild reaction conditions. Among these multicomponent transformations, [8] isocyanides involved Ugi four-component reactions (Ugi-4CR) [9] and the post functionalization of Ugi adducts [10,11] have been widely employed as highly efficient synthetic strategies for the access of multifunctional molecular architectures under mild reaction conditions. In 2014, Van der Eycken and coworkers furnished the first palladium catalyzed post-Ugi cascade cyclizations for the construction of spiroindolinone-isoindolinones (Scheme 1a).…”

Organocatalysis: A Tool of Choice for the Enantioselective Nucleophilic Dearomatization of Electron-Deficient Six-Membered Ring Azaarenium Salts

“…Whereas enantioselective hydride addition requires the use of pre-functionalized azaarenes (introduction of Nu prior to the addition of the hydride) and leads to tetrahydro products (and therefore will not be discussed herein) [7][8][9], nucleophilic dearomatization (Nu = H) offers the advantage of introducing chemical diversity Taking into account the above-mentioned challenges, enantioselective nucleophilic dearomatization of azaarenium salts has attracted a great deal of attention mostly by using metal catalysts with chiral ligands [11][12][13][14][15][16][17][18][19][20]. Nevertheless, in the last fifteen years and due to the advent of organocatalysis [21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36], which was recently highlighted through the Taking into account the above-mentioned challenges, enantioselective nucleophilic dearomatization of azaarenium salts has attracted a great deal of attention mostly by using metal catalysts with chiral ligands [11][12][13][14][15][16][17][18][19][20]. Nevertheless, in the last fifteen years and due to the advent of organocatalysis [21][22]…”

“…Nevertheless, in the last fifteen years and due to the advent of organocatalysis [21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36], which was recently highlighted through the Nobel Prize of Prof. B. List and Prof. D. MacMillan, several enantioselective organocatalytic dearomatization reactions of azaarenium salts have been reported [11,[13][14][15][16]18,19,37,38]. Organocatalysts can be classified following the mode of activation of either the electrophilic and/or nucleophilic partners involved in a given reaction [24,25].…”