Alkylidenation of esters on solid support and traceless synthesis of 2-substituted benzofurans

被引：30

作者：

Guthrie, EJ

Macritchie, J

Hartley, RC ^{[1
]}

机构：

[1] Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland

[2] Aventis Cropsci UK Ltd, Saffron Walden CB10 1XL, Essex, England

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 25期

基金：

英国工程与自然科学研究理事会;

关键词：

solid-phase synthesis; benzofurans; titanium and compounds; thioacetals;

D O I：

10.1016/S0040-4039(00)00753-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Polymer-supported esters are smoothly converted into enol ethers using a titanocene alkylidene prepared by treatment of 2-tert-butyldimethylsilyloxybenzaldehyde diphenyldithioacetal with the low valent titanium species Cp2Ti[P(OEt)(3)](2). Treatment of the enol ethers with acid leads to the release of ketones from the Wang resin in high yield. Traceless solid-phase synthesis of 2-substituted benzofurans is achieved in a three-step termination procedure. (C) 2000 Published by Elsevier Science Ltd.

引用

页码：4987 / 4990

页数：4

共 11 条

[1] Chameleon catches in combinatorial chemistry:: Tebbe olefination of polymer supported esters and the synthesis of amines, cyclohexanones, enones, methyl ketones and thiazoles [J].