Volume 32, Issue 18
Preparative Organic Chemistry
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ChemInform Abstract: Mesityllithium as a Reagent for Chemoselective Halogen—Lithium Exchange Reaction.

Yoshinori Kondo

Yoshinori Kondo

Grad. Sch. Pharm. Sci., Tohoku Univ., Aoba, Sendai 980, Japan

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Miho Asai

Miho Asai

Grad. Sch. Pharm. Sci., Tohoku Univ., Aoba, Sendai 980, Japan

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Tohru Miura

Tohru Miura

Grad. Sch. Pharm. Sci., Tohoku Univ., Aoba, Sendai 980, Japan

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Masanobu Uchiyama

Masanobu Uchiyama

Grad. Sch. Pharm. Sci., Tohoku Univ., Aoba, Sendai 980, Japan

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Takao Sakamoto

Takao Sakamoto

Grad. Sch. Pharm. Sci., Tohoku Univ., Aoba, Sendai 980, Japan

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First published: 27 May 2010

Abstract

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ChemInform Abstract

Mesityllithium is found to be an excellent lithiating agent for haloaromatics bearing alkoxycarbonyl groups to give chemoselectively aryllithiums which are further react with carbonyl compounds to give products (III), (V) and (VII), or undergo intramolecular 1,2-additions to give lactones (XI) and (XIII), the latter compound is a precursor for the camptothecin alkaloid.

chemical structure image

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