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

被引：4

作者：

Nambu, Hisanori ^{[1
,2
]}

Onuki, Yuta ^{[1
]}

Aso, Kana ^{[1
]}

Kanamori, Momoka ^{[1
]}

Tomohara, Keisuke ^{[2
]}

Tsuge, Kiyoshi ^{[3
]}

Yakura, Takayuki ^{[1
]}

机构：

[1] Univ Toyama, Fac Pharmaceut Sci, Sugitani, Toyama 9300194, Japan

[2] Kyoto Pharmaceut Univ, Lab Pharmaceut Mfg Chem, Kyoto 6078412, Japan

[3] Univ Toyama, Grad Sch Sci & Engn, Gofuku, Toyama 9308555, Japan

来源：

CHEMICAL COMMUNICATIONS | 2024年 / 60卷 / 34期

关键词：

OPENING CYCLIZATION; EFFICIENT SYNTHESIS; CYCLOPROPANE; CYCLOALKANE-1,3-DIONE-2-SPIROCYCLOPROPANES; DERIVATIVES; COMPOUND; STYRENES;

D O I：

10.1039/d3cc06033k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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. A novel method was devised for regioselective ring expansion of spirocyclopropanes to spirocyclobutanes with stabilized sulfonium ylides, affording 1,2-trans-disubstituted 6,8-dioxaspiro[3.5]nonane-5,9-diones without the formation of any isomers.

引用

页码：4537 / 4540

页数：5

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