Regioselective Functionalization of the Oxazole Scaffold Using TMP-Bases of Mg and Zn

被引：45

作者：

Haas, Diana ^{[1
]}

Mosrin, Marc ^{[2
]}

Knochel, Paul ^{[1
]}

机构：

[1] Univ Munich, Dept Chem, D-81377 Munich, Germany

[2] Bayer CropSci AG, D-65926 Frankfurt, Germany

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 24期

基金：

欧洲研究理事会;

关键词：

CENTER-DOT-LICL; CROSS-COUPLING REACTION; ALKENYLMAGNESIUM REAGENTS; GENERAL METHODOLOGY; PALLADIUM; ARYL; DERIVATIVES; METALATION; MAGNESIATION; ZINCATION;

D O I：

10.1021/ol403019c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general method for the synthesis of 2,4,5-trisubstituted oxazoles has been developed. Starting from commercially available oxazole, successive metalations using TMPMgCl center dot LiCl or TMPZnCl center dot LiCl led to the corresponding magnesiated or zincated species which were stable toward ring fragmentation. Furthermore, they readily reacted with various electrophiles, such as aryl and allylic halides, acid chlorides, TMSCl, and TMS-CN, providing highly functionalized oxazoles.

引用

页码：6162 / 6165

页数：4

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