76062-97-0Relevant articles and documents
A FACILE METHOD FOR PREPERATION OF THE OPTICALLY PURE 3-HYDROXYTETRADECANOIC ACID BY AN APPLICATION OF ASYMMETRICALLY MODIFIED NICKEL CATALYST
Tai, Akira,Nakahata, Masaaki,Harada, Tadao,Izumi, Yoshiharu,Kusumoto, Shoichi,et al.
, p. 1125 - 1126 (1980)
The enantioface-differentiating hydrogenation of methyl 3-oxotetradecanoate(R,R)-tartaric acid-NaBr-modified nickel gave methyl (R)-3-hydroxytetradecanoate(III) in 85percent e.e..After III was converted to dicyclohexylammonium salt of 3-hydroxytetradecanoic acid (I), the salt was recrystallized three times from acetonitrile and was then treated with acid to give optically pure (R)-I in a good yield.
Chiral Surfactant-Type Catalyst: Enantioselective Reduction of Long-Chain Aliphatic Ketoesters in Water
Lin, Zechao,Li, Jiahong,Huang, Qingfei,Huang, Qiuya,Wang, Qiwei,Tang, Lei,Gong, Deying,Yang, Jun,Zhu, Jin,Deng, Jingen
, p. 4419 - 4429 (2015/05/13)
A series of amphiphilic ligands were designed and synthesized. The rhodium complexes with the ligands were applied to the asymmetric transfer hydrogenation of broad range of long-chained aliphatic ketoesters in neat water. Quantitative conversion and excellent enantioselectivity (up to 99% ee) was observed for α-, β-, γ-, δ- and ε-ketoesters as well as for α- and β-acyloxyketone using chiral surfactant-type catalyst 2. The CH/π interaction and the strong hydrophobic interaction of long aliphatic chains between the catalyst and the substrate in the metallomicelle core played a key role in the catalytic transition state. Synergistic effects between the metal-catalyzed site and the hydrophobic microenvironment of the core in the micelle contributed to high stereoselectivity. (Chemical Equation Presented).
Enantioselective synthesis of α-amino acids from N-tosyloxy β-lactams derived from β-keto esters
Durham, Timothy B.,Miller, Marvin J.
, p. 27 - 34 (2007/10/03)
A novel synthetic sequence has been developed to convert simple β-keto esters into enantiomerically enriched α-amino acids. The key features of this sequence include the addition of azide to the C3 position of β-keto ester derived N-tosyloxy-β-lactams through a concomitant nucleophilic addition/N-O bond reduction reaction, a mild CsF-induced N1 benzylation of α-azido monocyclic β-lactams, the preparation of α-keto-β-lactams through a novel four-step sequence from the corresponding 3-azido-1-benzyl-β-lactams, and TEMPO-mediated ring expansion of these compounds to the corresponding N-carboxy anhydrides (NCAs). In addition, the synthesis, isolation, and characterization of unusual 3-imino and 3-chloramino-β-lactams is reported.
