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Synthesis
DOI: 10.1055/s-0043-1775471
DOI: 10.1055/s-0043-1775471
review
Synthesis of Spirocyclopropane Scaffolds: A Review
C.D.P. is grateful to the Ministry of Tribal Affairs (Scholarship Division), Government of India for a National Fellowship for Higher Education of Scheduled Tribe (ST) Students (202223-NFST-GUJ-00003).
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
Publication History
Received: 12 December 2024
Accepted after revision: 19 March 2025
Article published online:
04 June 2025
© 2025. Thieme. All rights reserved
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