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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
A Synthetic Method for Spirocyclobutanes via Ring Expansion of Donor-Acceptor Spirocyclopropanes with Stabilized
Kota Yoshioka1, Rika Sakai1, Hikaru Fujii1
1Laboratory of Pharmaceutical Synthetic Chemistry, Kyoto Pharmaceutical University, Kyoto 607-8412, Japan.
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.
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