Tandem PtCl2 catalyzed-thermal [3,3] rearrangements of enyne acetates

被引:63
作者
Cariou, K [1 ]
Mainetti, E [1 ]
Fensterbank, L [1 ]
Malacria, M [1 ]
机构
[1] Univ Paris 06, Lab Chim Organ, UMR 7611, CNRS, F-75252 Paris 05, France
关键词
enyne; cycloisomerization; flash chromatography;
D O I
10.1016/j.tet.2004.06.151
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,6 Enyne systems flanked with an acetate group at the propargyl position undergo tandem PtCl2-catalyzed-thermal [3,3] rearrangements leading to trienes. The scope of the transformation has been delineated by varying the nature of the alkynyl substituent R. For R=alkyl or phenyl, a direct 1,3-migration of the acetate group is proposed leading to an allenyl ester intermediate that undergoes a subsequent [3,3] rearrangement. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9745 / 9755
页数:11
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