2-METALATED OXAZOLES - PKA DEPENDENT DEUTERATIONS, NMR-STUDIES AND PALLADIUM-CATALYZED COUPLINGS

被引：50

作者：

CROWE, E ^{[1
]}

HOSSNER, F ^{[1
]}

HUGHES, MJ ^{[1
]}

机构：

[1] SMITHKLINE BEECHAM PHARMACEUT,HARLOW CM19 5AW,ESSEX,ENGLAND

来源：

TETRAHEDRON | 1995年 / 51卷 / 32期

关键词：

D O I：

10.1016/0040-4020(95)00498-W

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Deuteration experiments on 2-lithiated oxazoles show a pKa dependent regioselectivity suggesting that the ring cleaved tautomer dominates the equilibrium. Transmetallation to the zinc derivative gives a species which behaves as a C2 ring closed nucleophile as judged by deuteration and palladium catalysed coupling experiments. These conclusions are supported by nmr spectroscopy studies of the metallated species.

引用

页码：8889 / 8900

页数：12