Asymmetric Hydrogenation of α-Keto Phosphonates with Chiral Palladium Catalysts

Under atmospheric hydrogen pressure, a catalytic amount of palladium(II) trifluoroacetate and (R)-MeO-BIPHEP in 2,2,2-trifluoroethanol promoted the asymmetric hydrogenation of diisopropyl α-keto phosphonates 1 to afford the corresponding α-hydroxy phosphonates 2 in excellent yields and with a moderate enantioselectivities of up to 55 % ee. Racemic α-aryl-α-hydroxy phosphonates can be prepared by using palladium on carbon as the catalyst. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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