Practical synthesis of ynolate anions: naphthalene-catalyzed reductive lithiation of α,α-dibromo esters
✍ Scribed by Mitsuru Shindo; Ryoko Koretsune; Wakako Yokota; Kotaro Itoh; Kozo Shishido
- Book ID
- 104231846
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 64 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Reductive lithiation of a,a-dibromo esters using lithium naphthalenide afforded ester dianions leading to ynolate anions in good yields. Naphthalene-catalyzed reductive lithiation was also accomplished. This is a convenient, economical and practical method for the preparation of ynolate anions.
📜 SIMILAR VOLUMES
Ynolates have been synthesized via the thermally-inducedcleavage of ester dianions. The key intermediates, ester dianions, were generated from ~t -bromocarboxylic acid ester enolates via lithium halogen exchange, ot,~-Dibromocarboxylic acid ester also gives lithium amide free ynolates by addition of
Novel Synthesis of Ynolates via the Cleavage of Ester Dianions: α-Bromo and α,α-Dibromo Esters as Precursors. -Thermal cleavage of ester dianions generated from readily available α-bromo-and α,α-dibromo esters offers a new and convenient method to prepare lithium ynolates. The ynolates react with al