Enantioselective Hydrogenation Of β-Aryl-substituted (E)-β-Acetylaminoacrylate

Enantiomerically pureβ-amino acids are important chiral building blocks for the synthesis ofβ-peptides,β-lactam antibiotics, and many other important chiral drugs. For these reasons, enantioselective synthesis ofβ-amino acids has attracted extensive interest.Recently, the synthesis procedure ofβ-aryl-substituted (E)-β-acetylaminoacrylate has been proved wrong. After consulting a lot of literatures, this paper mainly realized the synthesis ofβ-aryl-substituted (E)-β-acetylaminoacrylate, and we also studied the hydrogenation ofβ-aryl-substituted (E)-β-acetylaminoacrylates catalyzed by Ru(OCOCH3)2[(R)-BINAP].1. We improved the synthetic method ofβ-aryl-substituted (E)-β-acetylaminoacrylates.2. We have investigated the hydrogenation ofβ-aryl-substituted (E)-β- acetylaminoacrylates catalyzed by Ru(OCOCH3)2[(R)-BINAP]. The influence of the reaction solvent, the pressure of H2, reaction temperature and the loading of catalyst on the reaction was studied in detail. The result showed that Ru(OCOCH3)2[(R)-BINAP] has good catalytic activity to this reaction, but the enantioselectivity of catalysts was moderate, which up to 80%ee.3. We studied the reaction of allylsamarium bromide withα,α-dihalo ketones. The product of this reaction is a type of multifunctional carbon compounds:α-hydroxy-α-allyl-aldehyde acetals. This method has the advantage of taking place in one pot, at room temperature and in high yields.