Synthesis of 2-acetoxy[5]helicene by sequential double aromatic oxy-Cope rearrangement

被引：27

作者：

Ogawa, Y

Ueno, T

Karikomi, M ^{[1
]}

Seki, K

Haga, K

Uyehara, T

机构：

[1] Utsunomiya Univ, Fac Engn, Dept Appl Chem, Utsunomiya, Tochigi 3218585, Japan

[2] Utsunomiya Univ, Ctr Instrumental Anal, Utsunomiya, Tochigi 3218585, Japan

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 43期

关键词：

aromatization; bridged bicyclic compound; aromatic oxy-Cope rearrangement; helicenes;

D O I：

10.1016/S0040-4039(02)01611-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of 2-acetoxy[5]helicene has been achieved by sequential double aromatic oxy-Cope rearrangement strategy. Combination of 1-methoxybicyclo[2.2.2]oct-5-en-2-one and p-bromophenylmagnesium bromide gave 3-bromophenanthrene through several steps including an aromatic oxy-Cope rearrangement as a key step. The second oxy-Cope rearrangement and the following transformation gave 2-acetoxy[5]helicene by similar procedure. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：7827 / 7829

页数：3

共 13 条

[1] Application of the Russig-Laatsch reaction to synthesize a bis[5]helicene chiral pocket for asymmetric catalysis [J].