Ring expansion of spirocyclopropanes with stabilized sulfonium ylides: highly diastereoselective synthesis of cyclobutanes

Hisanori Nambu; Yuta Onuki; Kana Aso; Momoka Kanamori; Keisuke Tomohara; Kiyoshi Tsuge; Takayuki Yakura

doi:10.1039/d3cc06033k

Ring expansion of spirocyclopropanes with stabilized sulfonium ylides: highly diastereoselective synthesis of cyclobutanes

Hisanori Nambu^*, Yuta Onuki, Kana Aso, Momoka Kanamori, Keisuke Tomohara, Kiyoshi Tsuge, Takayuki Yakura^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

A novel method was devised for regioselective ring expansion of Meldrum's acid-derived spirocyclopropanes to spirocyclobutanes with stabilized sulfonium ylides, affording 1,2-trans-disubstituted 6,8-dioxaspiro[3.5]nonane-5,9-diones in up to 87% yields without the formation of any isomers. The aforementioned reaction was also applied to the barbituric acid-derived spirocyclopropane, resulting in the formation of the corresponding cyclobutanes.

Original language	English
Pages (from-to)	4537-4540
Number of pages	4
Journal	Chemical Communications
Volume	60
Issue number	34
DOIs	https://doi.org/10.1039/d3cc06033k
State	Published - 2024/03/14

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Catalysis
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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title = "Ring expansion of spirocyclopropanes with stabilized sulfonium ylides: highly diastereoselective synthesis of cyclobutanes",

abstract = "A novel method was devised for regioselective ring expansion of Meldrum's acid-derived spirocyclopropanes to spirocyclobutanes with stabilized sulfonium ylides, affording 1,2-trans-disubstituted 6,8-dioxaspiro[3.5]nonane-5,9-diones in up to 87% yields without the formation of any isomers. The aforementioned reaction was also applied to the barbituric acid-derived spirocyclopropane, resulting in the formation of the corresponding cyclobutanes.",

author = "Hisanori Nambu and Yuta Onuki and Kana Aso and Momoka Kanamori and Keisuke Tomohara and Kiyoshi Tsuge and Takayuki Yakura",

note = "Publisher Copyright: {\textcopyright} 2024 The Royal Society of Chemistry.",

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doi = "10.1039/d3cc06033k",

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T1 - Ring expansion of spirocyclopropanes with stabilized sulfonium ylides

T2 - highly diastereoselective synthesis of cyclobutanes

AU - Nambu, Hisanori

AU - Onuki, Yuta

AU - Aso, Kana

AU - Kanamori, Momoka

AU - Tomohara, Keisuke

AU - Tsuge, Kiyoshi

AU - Yakura, Takayuki

PY - 2024/3/14

Y1 - 2024/3/14

N2 - A novel method was devised for regioselective ring expansion of Meldrum's acid-derived spirocyclopropanes to spirocyclobutanes with stabilized sulfonium ylides, affording 1,2-trans-disubstituted 6,8-dioxaspiro[3.5]nonane-5,9-diones in up to 87% yields without the formation of any isomers. The aforementioned reaction was also applied to the barbituric acid-derived spirocyclopropane, resulting in the formation of the corresponding cyclobutanes.

AB - A novel method was devised for regioselective ring expansion of Meldrum's acid-derived spirocyclopropanes to spirocyclobutanes with stabilized sulfonium ylides, affording 1,2-trans-disubstituted 6,8-dioxaspiro[3.5]nonane-5,9-diones in up to 87% yields without the formation of any isomers. The aforementioned reaction was also applied to the barbituric acid-derived spirocyclopropane, resulting in the formation of the corresponding cyclobutanes.

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U2 - 10.1039/d3cc06033k

DO - 10.1039/d3cc06033k

M3 - 学術論文

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AN - SCOPUS:85188543885

SN - 1359-7345

VL - 60

SP - 4537

EP - 4540

JO - Chemical Communications

JF - Chemical Communications

IS - 34

ER -

Ring expansion of spirocyclopropanes with stabilized sulfonium ylides: highly diastereoselective synthesis of cyclobutanes

Abstract

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