Abstract
Methyl 3-hydroxy-2-methylpropionate, known as the Roche ester, was prepared with high enantioselectivity (up to 96.7% ee) via the Rh-catalyzed asymmetric hydrogenation of methyl 2-hydroxymethylacrylate with a chiral 1,2,3,4-tetrahydro-1-naphthylamine-derived phosphine-phosphoramidite ligand (THNAPhos 5a) even at a low catalyst loading (0.1 mol %). An investigation on the substrate scope revealed that the ester group present in the substrate has a significant effect on the enantioselectivity, and the substrate with the bulkier ester group tended to give lower enantioselectivity.
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