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.

Highlights

  • Heterocyclic compounds are found in a broad range of bioactive molecules, natural products, and drugs

  • Asymmetric organocatalysis has appeared as an appealing tool in order to prepare such compounds with rich structural diversity and complexity through cascade, tandem, and domino processes [7,8,9]

  • The aim of this review is to describe recent advances towards the stereocontrolled synthesis of strained spiro-quaternary stereocenters on the oxindole core through non-covalent organocatalysis [14,15,16]

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Summary

Introduction

Heterocyclic compounds are found in a broad range of bioactive molecules, natural products, and drugs. Several novel efficient strategies based on catalytic methods have been validated to date for the direct assessment of such scaffolds in an enantiopure fashion [1,2,3] In this context, spirocyclic oxindole derivatives have appeared as privileged structural motifs being part of a great number of synthetic and natural products displaying remarkable biological activities as well as useful biomedical applications (Figure 1) [4,5,6]. After a quick overview about the Cinchona alkaloids (Section 1), Far to be exhaustive and comprehensive, the current review is divided according to the most the synthetic elaborations of thesethe natural-occurring are going to be Farsubsequent to be exhaustive and comprehensive, current revieworganocatalysts is divided according to the most employed class of catalysts.

Cinchona Alkaloid Catalysts
Based Catalysts
Thiourea-Based
Recent
Reaction
Michael
12. Synthesis
Double
15. Synthesis
Miscellaneous
Squaramide Catalysts
Double Michael Addition Sequence
21. Organocatalytic
22. Asymmetric
23. Organocatalysed
Conclusions
Findings
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