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
收藏
页码：6868 / 6871
页数：4
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