An unexpected equilibrium process associated with a standard approach to ynone synthesis

被引：51

作者：

Jackson, MM ^{[1
]}

Leverett, C ^{[1
]}

Toczko, JF ^{[1
]}

Roberts, JC ^{[1
]}

机构：

[1] GlaxoSmithKline, Chem Dev, Res Triangle Pk, NC 27709 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 14期

关键词：

D O I：

10.1021/jo025682i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A direct comparison between Weinreb amides and morpholine amides was made with regard to their reactions with alkynyllithium reagents to form ynones. While treatment with stoichiometric alkynyllithium generally effects complete reaction in the case of Weinreb amides, incomplete reactions are obtained from the corresponding morpholine amides. This difference is attributed to an unexpected equilibrium process in the latter case, and it is shown that the use of excess alkynyllithium reagent with morpholine, amides provides a synthetically useful synthesis of ynones at 0 degreesC.

引用

页码：5032 / 5035

页数：4

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