Abstract
A series of carbohydrate amphiphiles has been tested in the asymmetric hydrogenation of (Z)-methyl α-acetamidocinnamate using water as medium. Dependent on the chain length and the hydrophilicity of the head group an enhancement of activity and enantioselectivity of the [Rh(COD) 2]BF 4 + BPPM catalyst system could be observed. Sometimes the enantioselectivity exceeds that in methanol. The method used here is convenient and environmentally friendly because carbohydrates as amphiphiles are biologically degradable in water. Selected carbohydrate amphiphiles are able to transfer chirality onto the included substrate in a low manner (up to 6% ee). In these cases hydrogen bondings in the head group seem to be responsible for the effect of chiral induction.
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