Synthesis of Spirocyclopropane Scaffolds: A Review

Chirag D. Patel; Fouad Damiri; Mehul P. Parmar; Disha P. Vala; Mohammed Berrada; Hitendra M. Patel

doi:10.1055/s-0043-1775471

Synthesis, Table of Contents

Synthesis 2025; 57(14): 2131-2154
DOI: 10.1055/s-0043-1775471

review

Synthesis of Spirocyclopropane Scaffolds: A Review

Chirag D. Patel

^aDepartment of Chemistry, Sardar Patel University, Vallabh Vidyanagar-388 120, Gujarat, India

,

Fouad Damiri

^bLaboratory of Biology and Health, Faculty of Sciences Ben M’sick, University Hassan II of Casablanca, Casablanca 20000, Morocco

,

Mehul P. Parmar

^aDepartment of Chemistry, Sardar Patel University, Vallabh Vidyanagar-388 120, Gujarat, India

,

Disha P. Vala

^aDepartment of Chemistry, Sardar Patel University, Vallabh Vidyanagar-388 120, Gujarat, India

,

Mohammed Berrada

^bLaboratory of Biology and Health, Faculty of Sciences Ben M’sick, University Hassan II of Casablanca, Casablanca 20000, Morocco

,

Hitendra M. Patel ∗

^aDepartment of Chemistry, Sardar Patel University, Vallabh Vidyanagar-388 120, Gujarat, India

› Author Affiliations

Abstract

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Abstract

This review highlights different synthetic strategies for preparing a spirocyclopropane moiety, covering the literature from 1989 to 2024. The spirocyclopropane moiety is a structural scaffold that is used to access synthetic libraries of highly functionalized spirocarbo- and heterocyclic molecules. The review showcases different routes for the synthesis of spirocyclopropanes that utilize distinct precursors and methodologies, including cascade reactions, cyclopropanation, Michael-initiated ring closure (MIRC), and one-pot and multicomponent synthesis. These discussions are organized around the oxindole core, which include isatin, oxindole, 3-chlorooxindole, and 3-alkenyl oxindoles. Additionally, this review explores various ylides and other techniques. The goal of this review is to provide a background for synthetic chemistry researchers to develop new ideas and novel synthetic routes to spirocyclopropanes.

1 Introduction

2 Synthesis of Spirocyclopropanes from 3-Chlorooxindole Derivatives

3 Synthesis of Spirocyclopropanes from Isatin Derivatives

3.1 Synthesis of Spirocyclopropanes from Alkylidene Oxindole Derivatives

3.2 Synthesis of Spirocyclopropanes from Diazooxindole Compounds

4 Synthesis of Spirocyclopropanes from 1,3-Diones

5 Synthesis of Spirocyclopropanes from N-Ylides

6 Synthesis of Spirocyclopropanes from S-Ylides

7 Miscellaneous Syntheses of Spirocyclopropanes

8 Conclusion

9 List of Abbreviations

Key words

spirocyclopropanes - cyclopropanation - spirooxindoles

Full Text

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