Toward a better understanding on the mechanism of ortholithiation.: Tuning of selectivities in the metalation of meta-anisic acid by an appropriate choice of base

被引：27

作者：

Nguyen, TH

Chau, NTT

Castanet, AS

Nguyen, KPP

Mortier, J

机构：

[1] Univ Maine, Fac Sci, Unite Chim Organ Mol & Macromol, UMR 6011, F-72085 Le Mans, France

[2] CNRS, F-72085 Le Mans, France

[3] Univ Ho Chi Minh City, Ecole Sci Nat, Chim Organ Lab, Ho Chi Minh City, Vietnam

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 12期

关键词：

D O I：

10.1021/ol050761c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] If employed in THF at 0 degrees C, LTMP metalates meta-anisic acid at the doubly activated position. In contrast, n-BuLi/t-BuOK deprotonates position C-4 preferentially at low temperature. Functionalization at C-6 requires protection of the C-2 site beforehand. As a result of these findings, a new mechanism is proposed for the heteroatom-directed ortholithiation of aromatic compounds.

引用

页码：2445 / 2448

页数：4