Tetrahedron Letters p. 5193 - 5196 (1999)
Update date:2022-08-17
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An intramolecular hydride delivery process largely contributes during the double reduction of α-keto esters into diols by NaBH4. In the case of enolic α-keto esters, the first step of the process, the reduction of the keto group, occurred exclusively through an 1,2-hydride addition despite the predominance of the tautomeric enolic form. The clear-cut difference of reaction rate between enolic and non enolic substrate 4 for reaction carried out in methanol is interpreted in terms of competitive hydride consumption due to the extremely favorable reaction between this solvent and NaBH4.
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