Diastereoselective reduction of chiral α-ketoamides derived from (S)-proline esters with sodium borohydride. Preparation of optically active α-hydroxy acids
- 1 January 1985
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 769-772
- https://doi.org/10.1039/p19850000769
Abstract
Diastereoselective reductions of chiral α-ketoamides (3) derived from (S)-proline esters (2) with sodium borohydride were examined. Hydrolysis of the reduction products afforded optically active α-hydroxy acids (5) in good enantiomeric excesses (e.e.). The most influential factor of the asymmetric induction was the effect of using a mixed hydroxylic and non-hydroxylic solvent. The degree of asymmetric induction varied considerably with the ratio of alcohol and tetrahydrofuran (THF) in the mixed solvent. With aromatic ketoamides (3), higher asymmetric induction occurred in a mixed alcohol–THF solvent than in the corresponding individual solvents.Keywords
This publication has 0 references indexed in Scilit: