530103-60-7

Upstream product

• 4783-65-7 N-benzyl-2-piperidinone 
• 79-20-9 acetic acid methyl ester 

Downstream Products

• 565230-21-9 N-[1-(3-benzyl-2-oxo-3-azacyclohexylidene)ethyl]-L-valine diethylamide 
• 610253-85-5 rac-3-acetyl-1-benzyl-3-(3-oxobutyl)-2-piperidone 
• 565230-24-2 (S)-N-(8-benzyl-3-methyl-7-oxo-8-azaspiro[5.5]undec-2-en-1-ylidene)-L-valine diethylamide 

Relevant academic research and scientific papers

Dynamic Kinetic Asymmetric Reductive Amination: Synthesis of Chiral Primary β-Amino Lactams

A highly efficient ruthenium-catalyzed asymmetric reductive amination (ARA) of racemic β-keto lactams with molecular hydrogen and ammonium salts is disclosed for the synthesis of enantiomerically pure primary amino lactams through dynamic kinetic resolution (DKR). By this approach, a range of syn primary β-amino lactams were obtained in high yields with high chemo-, enantio-, and diastereoselectivity (up to 98 % yield, 99 % ee, >20:1 d.r., syn products). The utility of the products has been demonstrated by rapid access to a key synthetic intermediate towards biologically active drug molecules. Meanwhile, mechanistic studies and control experiments indicate that the reaction may proceed through the hydrogenation of an iminium intermediate.

Iridium-catalyzed asymmetric hydrogenation of racemic β-keto lactams via dynamic kinetic resolution

A highly efficient Ir-catalyzed asymmetric hydrogenation of racemic β-keto lactams via dynamic kinetic resolution (DKR) for the synthesis of optically active β-hydroxyl lactams has been described. With the Ir-SpiroSAP catalyst, a series of racemic β-keto lactams including β-keto γ-, δ-, and ?-lactams were hydrogenated to chiral β-hydroxy lactams in high yields (87-99%) with excellent enantio- and diastereoselectivity (83-99.9% ee, syn/anti: 97:3->99:1) at low catalyst loading under mild reaction conditions. This efficient method has been successfully applied in the synthesis of the chiral intermediate of fluoroquinolone antibiotic premafloxacine.

Preparation of acyloins by cerium-catalyzed, direct hydroxylation of β-dicarbonyl compounds with molecular oxygen

We report the metal-catalyzed α-hydroxylation of a variety of cyclic and acyclic β-dicarbonyl compounds by molecular oxygen. The decisive advantage of this new method is the use of catalytic amounts of the nontoxic cerium salt CeCl3·7H2O in 2-propanol at ambient temperature. Most of the cyclic substrates 4a-4i give high yields of analytically pure products 5a-5i, and the workup procedure is simple filtration through silica gel. The oxidation of acyclic dicarbonyl compounds 4j-4p, however, is accompanied by side reactions and decomposition, reducing the yields of products 5j-5p significantly. A proposed mechanism is in agreement with experimental results, in particular the observed oxygen uptake. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.