Reagent-controlled regioselective [3,3]-sigmatropic rearrangement of N-trifluoroacetyl enehydroxylamine and its synthetic application

被引：5
|
作者：
Takeda, Norihiko [1 ]
Miyata, Okiko [1 ]
Kitamura, Maria [1 ]
Kagehira, Shunsuke [1 ]
Naito, Takeaki [1 ]
机构：
[1] Kobe Pharmaceut Univ, Kobe, Hyogo 6588558, Japan
来源：
SYNLETT | 2006年 / 20期
关键词：
benzofuran; enehydroxylamine; 3,3]-sigmatropic rearrangement; lunarine; galanthamine;
D O I：
10.1055/s-2006-958431
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Regioselective [3,3]-sigmatropic rearrangement provides a novel method for the construction of hexahydrodibenzofuran with a quaternary carbon in the ring juncture. Upon treatment with TFAA. oxime ethers carrying an electron-withdrawing group smoothly underwent regioselective rearrangement to give the hexahydrodibenzofuran with a quaternary carbon. On the other hand, the reaction of oxime ethers with TFAT-DMAP gave tetrahydrodibenzofurans carrying a substituent at the 4-position. The hexahydrodibenzofuran with a quaternary carbon was effectively converted into a key intermediate for lunarine synthesis.
引用
收藏
页码：3415 / 3418
页数：4
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