Metal-mediated two-atom carbocycle enlargement in aqueous medium

被引：43

作者：

Li, CJ ^{[1
]}

Chen, DL ^{[1
]}

Lu, YQ ^{[1
]}

Haberman, JX ^{[1
]}

Mague, JT ^{[1
]}

机构：

[1] Tulane Univ, Dept Chem, New Orleans, LA 70118 USA

来源：

TETRAHEDRON | 1998年 / 54卷 / 11期

关键词：

D O I：

10.1016/S0040-4020(98)00004-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The indium and tin-mediated carbonyl allylations of 1,3-dicarbonyl compounds have been studied in aqueous medium. The study led to the development of a novel two-atom carbocycle-enlargement in water. Five-, six-, seven-, eight-, and twelve-membered rings are enlarged by two carbon atoms into seven-, eight-, nine-, ten-, and fourteen-membered ring derivatives respectively. Tetralone derivatives are similarly expanded to 6-8 fused ring systems; and indanone derivatives are expanded to 5-7 fused ring systems. The use of both indium and zinc as the metal mediators provided the ring expansion products successfully. The use of water ar a solvent was found to be essential for the ring expansion reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2347 / 2364

页数：18

共 67 条

[1] CECL3-MEDIATED ADDITION OF GRIGNARD-REAGENTS TO 1,3-DIKETONES [J].