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Mechanistic rationale for the NaBH4 reduction of α-keto esters

✍ Scribed by V. Dalla; J.P. Catteau; P. Pale

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
261 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

An intrumolecular hydride delivery process largely contributes during the double reduction of a-keto esters into diols by NaBH4. In the case of enolic a-keto esters, the first step of the process, the reduction of the keto group, oecured exclusively through an 1,2-hydride addition despite the predomimmce of the teutomeric cnolic form. The clear-cut difference of reaction rate between cnolic and non coolie subslrute 4 for reaction carried out in methanol is interpreted in terms of competitive hydride consumption due to the ext~anely favorable reaction between this solvent and NaBH4.

📜 SIMILAR VOLUMES

Chemocontrolled reduction of aromatic α-
Chemocontrolled reduction of aromatic α-ketoesters by NaBH4: Selective synthesis of α-hydroxy esters or 1,2-diols
✍ Vincent Dalla; Philippe Cotelle; Jean Pierre Catteau 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 261 KB

ot-hydroxyesters 5a.g or diols 6a.g have been obtained in high yields by reduction of aromatic ot-ketoesters 4 once or twice respectively by using NaBH4 as the reducer under suitable conditions. The use of a solvent that does not interact with the reagent allowed the double reduction to occur with o