Base-catalyzed one-pot synthesis of dispiro-1,3-dioxolane bisoxindoles from N-methylisatin and methyl propiolate

被引：15

作者：

Kim, Su Yeon ^{[1
]}

Roh, Hwa Jung ^{[1
]}

Seo, Da Young ^{[1
]}

Ryu, Ji Yeon ^{[1
]}

Lee, Junseong ^{[1
]}

Kim, Jae Nyoung ^{[1
]}

机构：

[1] Chonnam Natl Univ, Dept Chem & Inst Basic Sci, Gwangju 500757, South Korea

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 10期

基金：

新加坡国家研究基金会;

关键词：

Bisoxindoles; 1,3-Dioxolanes; Isatin; Methyl propiolate; ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS; HIGHLY DIASTEREOSELECTIVE SYNTHESIS; MICHAEL-ALDOL REACTIONS; DIELS-ALDER REACTION; ENANTIOSELECTIVE CONSTRUCTION; STEREOSELECTIVE CONSTRUCTION; SPIROCYCLOPENTANE BIOXINDOLES; 1,3-DIPOLAR CYCLOADDITION; CYCLIZATION-CARBONYLATION; SPIROCYCLIC OXINDOLES;

D O I：

10.1016/j.tetlet.2017.01.055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Base-catalyzed domino reaction between N-methylisatin and methyl propiolate afforded four diastereomeric dispiro-1,3-dioxolane bisoxindoles. The reaction mechanism involved sequential 1,2-addition of acetylide anion to the carbonyl group of isatin, 1,2-addition of the resulting oxyanion to a second molecule of isatin, and the final 5-exo-dig cyclization process.

引用

页码：914 / 918

页数：5

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