LrgpV1, Main, Exploration, bibRecord, 001372

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.

Identifieur interne : 001372 ( Main/Exploration ); précédent : 001371; suivant : 001373

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.

Auteurs : Thi-Huu Nguyen [France] ; Nguyet Trang Thanh Chau ; Anne-Sophie Castanet ; Kim Phi Phung Nguyen ; Jacques Mortier

Source :

Organic letters [ 1523-7060 ] ; 2005.

RBID : pubmed:15932219

Descripteurs français

KwdFr :
- Acide vanillique (), Acide vanillique (analogues et dérivés), Chimie organique (), Composés organométalliques (), Lithium (), Stéréoisomérie, Température, Thermodynamique.
MESH :
- analogues et dérivés : Acide vanillique.
- Acide vanillique, Chimie organique, Composés organométalliques, Lithium, Stéréoisomérie, Température, Thermodynamique.

English descriptors

KwdEn :
- Chemistry, Organic (methods), Lithium (chemistry), Organometallic Compounds (chemistry), Stereoisomerism, Temperature, Thermodynamics, Vanillic Acid (analogs & derivatives), Vanillic Acid (chemistry).
MESH :
- chemical , analogs & derivatives : Vanillic Acid.
- chemical , chemistry : Lithium, Organometallic Compounds, Vanillic Acid.
- methods : Chemistry, Organic.
- Stereoisomerism, Temperature, Thermodynamics.

Abstract

[reaction: see text] 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.

DOI: 10.1021/ol050761c
PubMed: 15932219

Affiliations:

Le document en format XML

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<front><div type="abstract" xml:lang="en">[reaction: see text] 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.</div>
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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.

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.

Source :

Descripteurs français

English descriptors

Abstract

Links toward previous steps (curation, corpus...)

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