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

页码：3415 / 3418

页数：4

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