A new reagent system for installation of an aryl group onto the monoacetate of 4-cyclopentene-1,3-diol

被引：20

作者：

Ainai, T ^{[1
]}

Ito, M ^{[1
]}

Kobayashi, Y ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 2268501, Japan

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 20期

关键词：

coupling reaction; 4-cyclopentene-1,3-diol monoacetate; Grignard reagent; copper catalyst; dihydromultifidene;

D O I：

10.1016/S0040-4039(03)00777-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Among the three types of reagents from PhMgX (X=Br, Cl) and CuCN for phenylation of 4-cyclopentene-1,3-diol monoacetate, PhMgCl/CuCN (cat.) and Ph2Cu(CN)(MgCl)(2) in THF afforded the trans- 1,4-isomer efficiently (82-87% yields, 91-93% regioselectivity). Similarly, o- and p-RC6H4MgCl (R = Me, OMe, CH2=CH) in combination with CuCN furnished good to excellent reactivity and regioselectivity. As an application, a three-step synthesis of dihydromultifidene was accomplished successfully. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：3983 / 3986

页数：4

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