Rhodium-catalyzed enantioselective and diastereoselective hydrogenation of β-ketoenamides: Efficient access to anti 1,3-amino alcohols

Valuable chiral building blocks were synthesized with excellent enantioselectivity and diastereoselectivity through tandem hydrogenation of (Z)-β-ketoenamides, which were in turn prepared by the direct condensation of 1,3- diketones with acetamide (see scheme). The chiral amino alcohol products can be converted into useful γ-aryl isobutylamines through hydrogenolysis with Pd/C. R1=aryl, heteroaryl, methyl; R2=alkyl. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.