An efficient synthesis of cycloalkane-1,3-dione-2-spirocyclopropanes from 1,3-cycloalkanediones using (1-aryl-2-bromoethyl)-dimethylsulfonium bromides: application to a one-pot synthesis of tetrahydroindol-4(5H)-one

被引：27

作者：

Nambu, Hisanori ^{[1
]}

Fukumoto, Masahiro ^{[1
]}

Hirota, Wataru ^{[1
]}

Ono, Naoki ^{[1
]}

Yakura, Takayuki ^{[1
]}

机构：

[1] Toyama Univ, Grad Sch Med & Pharmaceut Sci, Sugitani, Toyama 9300194, Japan

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 29期

关键词：

Cyclopropane; 1,3-Cyclohexanediones; Sulfonium salts; Indole; One-pot synthesis; RHODIUM-CATALYZED CYCLOPROPANATION; SUBSTITUTED VINYLSULFONIUM SALTS; BROMODIMETHYLSULFONIUM BROMIDE; ASYMMETRIC CYCLOPROPANATION; ACTIVATED CYCLOPROPANES; ALKENES; REAGENTS; ROUTE; CYCLOADDITION; DIHYDROFURANS;

D O I：

10.1016/j.tetlet.2015.05.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of cyclohexane- and cyclopentane-1,3-dione-2-spirocyclopropanes from 1,3-cycloalkanediones using sulfonium salts was achieved. The reaction of 1,3-cycloalkanediones with (1-aryl-2-bromoethyl)-dimethylsulfonium bromides and powdered K2CO3 in EtOAc provided the corresponding spirocyclopropanes in high yields. Furthermore, a one-pot synthesis of tetrahydroindol-4(5H)-one from 1,3-cyclohexanedione was achieved using the present protocol and a sequential ring-opening cyclization of spirocyclopropane with a primary amine. (c) 2015 Elsevier Ltd. All rights reserved.

引用

页码：4312 / 4315

页数：4

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