143129-53-7

Upstream product

• 5291-77-0 1-benzyl-2-pyrrolidone 
• 79-20-9 acetic acid methyl ester 

Downstream Products

• 143129-49-1 (S)-1-benzyl-3-((R)-1-hydroxyethyl)pyrrolidin-2-one 
• 161011-00-3 N-{(1S)-1-[(3R)-1-benzylpyrrolidin-3-yl]ethyl}-N-methylamine 
• 143129-60-6 (3R,1'R)-1-benzyl-3-[(1'-hydroxy)ethyl]pyrrolidine 
• 163659-01-6 1-benzyl-3-(S)-(1-(S)-tert-butoxycarbonylaminoethyl)pyrrolidine 

Relevant academic research and scientific papers

Facile Synthesis of Spirocyclic Lactams via [3+2] and [3+3] Aza-Annulation Reactions

Spirocyclic pyrrolidones and piperidones were synthesized starting from readily available α-ketolactones and α-ketolactams employing [3+2]- and [3+3]-aza-annulation reactions. Annulation reactions proceeded with good yields and further reduction of the ex

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.