A new enantioselective synthesis of glycidates via dynamic kinetic resolution of racemic 2-chloro-3-keto esters using chiral Ru (II) complexes

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A new enantioselective synthesis of glycidates via dynamic kinetic resolution of racemic 2-chloro-3-keto esters using chiral Ru (II) complexes

Genêt, Jean-Pierre; Caño de Andrade, M.C.; Ratovelomanana-Vidal, V.

Tetrahedron letters, 03/1995, Volume: 36, Issue: 12

Journal Article

Graphic 2-chloro-3-keto esters were quantitatively hydrogenated to syn and anti 2-chloro-3-hydroxyester by asymmetric hydrogenation with chiral ruthenium (II) catalysis prepared in-situ from (COD)Ru(2-Methylallyl) 2 in presence of atropisomeric ligands such as MeO-Biphep and Binap, giving enantioselectivity up to 99%. 2-chloro-3-hydroxy esters were treated with different bases to give (E)- and (Z)-2,3-epoxyalkanoates in 65–90% yields with 84–97% ee.

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Genêt, Jean-Pierre | Caño de Andrade, M.C. | Ratovelomanana-Vidal, V.

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