A Synthetic Method for Spirocyclobutanes via Ring Expansion of Donor–Acceptor Spirocyclopropanes with Stabilized Sulfonium Ylides

A sulfonium ylide-mediated ring expansion of donor-acceptor spirocyclopropanes has been developed to provide access to spirocyclobutanes. Spirocyclopropanes derived from 1,3-indandione undergo efficient ring expansion with stabilized sulfonium ylides, affording the corresponding spirocyclobutanes as single isomers in high yield. Given that spirocyclic frameworks, with their rigid three-dimensional architecture, play a key role in drug discovery, spirocyclobutanes represent particularly promising core structures. This synthetic method is expected to make a significant contribution to pharmaceutical development.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-05-10
DOI
https://doi.org/10.1021/acs.joc.6c00210
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
0.00
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article

A Synthetic Method for Spirocyclobutanes via Ring Expansion of Donor–Acceptor Spirocyclopropanes with Stabilized Sulfonium Ylides

Hisanori Nambu, Kōta Yoshioka, Keisuke Tomohara, Rika Sakai et al.
The Journal of Organic Chemistry
Cyclopropane Reaction Mechanisms
article

A Synthetic Method for Spirocyclobutanes via Ring Expansion of Donor–Acceptor Spirocyclopropanes with Stabilized Sulfonium Ylides

Hisanori Nambu, Kōta Yoshioka, Keisuke Tomohara, Rika Sakai, Hikaru Fujii
article en

Abstract

A sulfonium ylide-mediated ring expansion of donor-acceptor spirocyclopropanes has been developed to provide access to spirocyclobutanes. Spirocyclopropanes derived from 1,3-indandione undergo efficient ring expansion with stabilized sulfonium ylides, affording the corresponding spirocyclobutanes as single isomers in high yield. Given that spirocyclic frameworks, with their rigid three-dimensional architecture, play a key role in drug discovery, spirocyclobutanes represent particularly promising core structures. This synthetic method is expected to make a significant contribution to pharmaceutical development.

The Journal of Organic Chemistry
Kyoto Pharmaceutical University (JP), State Key Laboratory of Synthetic Chemistry (CN)
Openalex Percentile: Top 9%
Cyclopropane Reaction Mechanisms
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A Synthetic Method for Spirocyclobutanes via Ring Expansion of Donor–Acceptor Spirocyclopropanes with Stabilized Sulfonium Ylides — Hisanori Nambu, Kōta Yoshioka, et al. · The Journal of Organic Chemistry (2026) | TGRS Research Map | TGRS