An efficient synthesis of 3-trifluoromethylated 8-oxabicyclo[3.2.1]octa-2,6-dienes

被引：21
作者：
Wang, YL
Zhu, SZ
Zhu, GY
Huang, QC
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
[2] Peking Univ, Dept Chem, Beijing 100871, Peoples R China
来源：
TETRAHEDRON | 2001年 / 57卷 / 34期
基金：
中国国家自然科学基金;
关键词：
trifluoromethyl; vinyldiazo compounds; furans; carbenoids; rhodium(II) acetate; 3+4] annulation;
D O I：
10.1016/S0040-4020(01)00709-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The rhodium(II) acetate catalyzed decomposition of 3-trifluoromethylated vinyldiazomethanes 3 in the presence of furans resulted in the formation of a series of 3-trifluoromethylated 8-oxabicyclo[3.2.1]octa-2,6-dienes. The 4-substituent on the vinyldiazomethanes had great effects on the product distribution and the stereo- and regiochemistry of the [3+4] annulation products. The rhodium(II) acetate catalyzed reaction of 4-carbonyl substituted vinyldiazomethanes 3a-c with furans resulted in cyclopropenes and [3+4] annulation products, while in the case of cyano-substituted vinyldiazomethanes 3d, only cycloaddition products were obtained. The reaction was presumed to follow a tandem cyclopropanation/Cope rearrangement mechanism. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：7337 / 7342
页数：6
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