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

delete2026-05-10
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PRE
AI
K
Kōta Yoshioka
R
Rika Sakai
H
Hikaru Fujii
K
Keisuke Tomohara
H
Hisanori Nambu *
DOI:10.1021/acs.joc.6c00210delete
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Abstract

Abstract

En 中文
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.
Keywords:
spirocyclobutanes
ring expansion
sulfonium ylide
donor–acceptor spirocyclopropanes
synthetic method

Journal

T
The Journal of Organic Chemistry
IF:
3.6
Papers:
1.4K
Citations:
2

Organization

Kyoto Pharmaceutical University cover
Kyoto Pharmaceutical University
Scholars:
1.6K
Papers: 883
Citations: 1.4K