Rhodium-Catalyzed Ring Expansion of Cyclopropanes to Seven-membered Rings by 1,5 C-C Bond Migration

被引：44

作者：

Li, Xiaoxun ^{[1
]}

Zhang, Min ^{[1
]}

Shu, Dongxu ^{[2
]}

Robichaux, Patrick J. ^{[2
]}

Huang, Suyu ^{[1
]}

Tang, Weiping ^{[1
]}

机构：

[1] Univ Wisconsin, Sch Pharm, Madison, WI 53705 USA

[2] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 44期

关键词：

C-C migration; cyclopropane; isomerization; rhodium; ring expansion; VINYLCYCLOPROPANE-CYCLOPENTENE REARRANGEMENT; INTRAMOLECULAR 5+2 CYCLOADDITIONS; METAL CARBENE TRANSFORMATIONS; ASYMMETRIC 4+1 CYCLOADDITION; HOMOGENEOUS GOLD CATALYSIS; EFFICIENT SYNTHESIS; PROPARGYLIC ESTERS; THERMAL REARRANGEMENTS; CLAISEN REARRANGEMENT; ORGANIC-SYNTHESIS;

D O I：

10.1002/anie.201104861

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The golden side of rhodium: Highly functionalized seven-membered rings were prepared from substituted cyclopropanes by a Rh I-catalyzed tandem isomerization reaction. The π-acidic Rh I catalyst promoted the formation of an allene intermediate by a 1,3 acyloxy migration of a propargyl ester and a subsequent net 1,5 migration of a cyclopropane C-C bond. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：10421 / 10424

页数：4

共 119 条

[1] Gold-catalyzed addition of carbon nucleophiles to propargyl carboxylates [J].