Gold-Catalyzed 1,3-Acyloxy Migration/5-exo-dig Cyclization/1,5-Acyl Migration of Diynyl Esters

被引：85

作者：

Leboeuf, David ^{[1
]}

Simonneau, Antoine ^{[1
]}

Aubert, Corinne ^{[1
]}

Malacria, Max ^{[1
]}

Gandon, Vincent ^{[2
]}

Fensterbank, Louis ^{[1
]}

机构：

[1] UPMC Paris 06, IPCM UMR CNRS 7201, F-75252 Paris 05, France

[2] Univ Paris 11, UMR CNRS 8182, F-91405 Orsay, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 30期

关键词：

cycloisomerization; diynes; gold; homogeneous catalysis; CYCLOISOMERIZATION; ACCESS; ACTIVATION; ENYNES;

D O I：

10.1002/anie.201101179

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Working three shifts: Polyconjugated δ-diketones are formed stereoselectively in high yields by the gold-catalyzed rearrangement of 1,6-diyn-3-yl esters. This cascade involves a 1,3-sigmatropic acyloxy shift, a 5-exo-dig cyclization of the resulting allenyne, and an unprecedented 1,5-sigmatropic shift of an acyl fragment. The usefulness of the products was shown by an efficient acid-catalyzed transformation into a complex polycyclic framework. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：6868 / 6871

页数：4

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