Boron trichloride mediated regioselective claisen rearrangement of resorcinol derivatives: Application to resorcinol carvonyl ethers

被引：13

作者：

Ito, Fumihiro ^{[1
]}

Fusegi, Keiko ^{[1
]}

Kumamoto, Takuya ^{[1
]}

Ishikawa, Tsutomu ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan

来源：

SYNTHESIS-STUTTGART | 2007年 / 12期

关键词：

carvone; boron trichloride; rearrangement; regioselectivity; resorcinol;

D O I：

10.1055/s-2007-983712

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Claisen rearrangement (CR) of resorcinol allyl ethers was examined. Although thermal CR gave low regioselectivity, the selectivity was much improved in the presence of a Lewis acid such as boron trichloride. This rearrangement was successfully applied to resorcinol carvonyl ethers for the regioselective introduction of a carvone unit into the resorcinol skeleton for the synthesis of phytoestrogenic miroestrols.

引用

页码：1785 / 1796

页数：12

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