Non-Covalent Organocatalyzed Domino Reactions Involving Oxindoles: Recent Advances

Abstract

The ubiquitous presence of spirooxindole architectures with several functionalities and stereogenic centers in bioactive molecules has been appealing for the development of novel methodologies seeking their preparation in high yields and selectivities. Expansion and refinement in the field of asymmetric organocatalysis have made possible the development of straightforward strategies that address these two requisites. In this review, we illustrate the current state-of-the-art in the field of spirooxindole synthesis through the use of non-covalent organocatalysis. We aim to provide a concise overview of very recent methods that allow to the isolation of unique, densely and diversified spirocyclic oxindole derivatives with high structural diversity via the use of cascade, tandem and domino processes.

Novel pseudopolymeric magnetic nanoparticles as a hydrogen bond catalyst for the synthesis of tetrahydrodipyrazolopyridine derivatives under mild reaction conditions

“…[2,3] Therefore, it is no wonder that hydrogen-bonding organocatalysis as a fascinating study topic expanded rapidly, and several review articles deal with this area of catalysis. [4][5][6][7][8][9][10] Recently, we have reviewed various aspects of urea and its derivatives as powerful and influential H-bonding catalytic active agents in a wide range of chemical processes. [11] Although homogenous catalytic systems represent many practical benefits like high activity and selectivity, but, due to the high costs and troubles in catalyst separation and recovering processes, the efficacious performance of them is hindered.…”

Double Spirocyclization of Arylidene-Δ2-Pyrrolin-4-Ones with 3-Isothiocyanato Oxindoles

“…In this context, organocatalysis has emerged as a powerful synthetic tool for the preparation of complex molecular architectures from simple starting materials, especially due to its operational simplicity, easily available catalysts, and benign reaction conditions [11][12][13][14][15][16][17][18][19][20][21]. 3-Isothiocyanato oxindoles, possessing both the nucleophilic and the electrophilic reaction site, represent a convenient building block for the cascade construction of diverse heterocyclic systems [22][23][24][25]. These transformations can be conducted under mild organocatalytic conditions in a highly stereoselective manner.…”

Convenient access to pyrrolidin-3-ylphosphonic acids and tetrahydro-2H-pyran-3-ylphosphonates with multiple contiguous stereocenters from nonracemic adducts of a Ni(II)-catalyzed Michael reaction

“…Moreover, the generation of the first stereocenter of a given configuration during the catalytic process leads to the possibility of creating enantiomerically pure compounds with several stereocenters through the directed regulation of diastereoselectivity in subsequent transformations, which can be realized as stepwise or cascade processes. Due to this reason, the Michael reaction was successfully used over the last decade to synthesize a wide range of heterocycles [33][34][35][36][37][38][39][40][41][42][43][44]. 2-Oxo-4-nitrophosphonates [45,46], the Michael adducts of β-keto phosphonates and nitroolefins, can be considered as versatile reagents for the synthesis of various phosphoryl-substituted heterocycles.…”