Metalated carboxylic acids. II. Monoalkylation of metalated toluic acids and dimethylbenzoic acids

TL;DR: The methoxymethoxy substituent when attached to an aromatic ring functions as a moderately strong ortho-directing group in hydrogen-metal exchange reactions as mentioned in this paper, and the propensity of the methoxylated arene toward ring metallation is greatly enhanced with concomitant suppression of undesirable side reactions such as nucleophilic attack and addition of the metallating species.

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Directed Ortho-Metalation of Unprotected Benzoic Acids. Methodology and Regioselective Synthesis of Useful Contiguously 3- and 6-Substituted 2-Methoxybenzoic Acid Building Blocks

Thi-Huu Nguyen, +2 more

- 21 Jan 2006 -

Organic Letters

TL;DR: By treatment with s-BuLi/TMEDA at -78 degrees C, unprotected 2-methoxybenzoic acid is deprotonated exclusively in the position ortho to the carboxylate and a reversal of regioselectivity is observed when the acid is treated with n-Bu Li/t-BuOK.

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Deracemization by enantioselective protonation IV an improved method for the enantiomeric enrichment of α-aminoacids using metalation by means of chiral amides

Lucette Duhamel, +1 more

- 01 Jan 1980 -

Tetrahedron Letters

TL;DR: Optically active α-aminoesters are obtained by metalation of the corresponding Schiff bases by chiral lithium amide followed by protonation by an achiral or a chiral acid as discussed by the authors.

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Enantioselective deprotonation of two racemic cyclic carbonyl compounds by a chiral lithium amide

M.B. Eleveld, +1 more

- 01 Jan 1986 -

Tetrahedron Letters

TL;DR: In this article, the cyclic carbonyl compounds 2 and 8 have been obtained in optical active form (o. y. 46% and 36%, respectively) from the racemic compounds by a deprotonation/protonation sequence using chiral lithium amide 1.

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