898753-83-8Relevant academic research and scientific papers
Nickel-Catalyzed Synthesis of Dialkyl Ketones from the Coupling of N-Alkyl Pyridinium Salts with Activated Carboxylic Acids
Hoerrner, Megan E.,Wang, Jiang,Watson, Mary P.,Weix, Daniel J.
supporting information, p. 13484 - 13489 (2020/06/10)
While ketones are among the most versatile functional groups, their synthesis remains reliant upon reactive and low-abundance starting materials. In contrast, amide formation is the most-used bond-construction method in medicinal chemistry because the che
Ketones from Nickel-Catalyzed Decarboxylative, Non-Symmetric Cross-Electrophile Coupling of Carboxylic Acid Esters
Wang, Jiang,Cary, Brian P.,Beyer, Peyton D.,Gellman, Samuel H.,Weix, Daniel J.
, p. 12081 - 12085 (2019/08/12)
Synthesis of the C?C bonds of ketones relies upon one high-availability reagent (carboxylic acids) and one low-availability reagent (organometallic reagents or alkyl iodides). We demonstrate here a ketone synthesis that couples two different carboxylic acid esters, N-hydroxyphthalimide esters and S-2-pyridyl thioesters, to form aryl alkyl and dialkyl ketones in high yields. The keys to this approach are the use of a nickel catalyst with an electron-poor bipyridine or terpyridine ligand, a THF/DMA mixed solvent system, and ZnCl2 to enhance the reactivity of the NHP ester. The resulting reaction can be used to form ketones that have previously been difficult to access, such as hindered tertiary/tertiary ketones with strained rings and ketones with α-heteroatoms. The conditions can be employed in the coupling of complex fragments, including a 20-mer peptide fragment analog of Exendin(9–39) on solid support.
Synthesis of γ-, δ-, and ε-lactams by asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)iminoesters
Guijarro, David,Pablo, Oscar,Yus, Miguel
, p. 3647 - 3654 (2013/05/22)
Highly enantiomerically enriched γ- and δ-lactams have been prepared by a simple and very efficient procedure that involves the asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)iminoesters followed by desulfinylation of the nitrogen atom and spo
4-(trans-4-methylcyclohexyl)-4-oxobutyric acid (JTT-608). A new class of antidiabetic agent
Shinkai, Hisashi,Ozeki, Hidekazu,Motomura, Takahisa,Ohta, Takeshi,Furukawa, Noboru,Uchida, Itsuo
, p. 5420 - 5428 (2007/10/03)
During an investigation of drugs for improving the β-cell response to glucose, we found that 4-cyclohexyl-4-oxobutyric acid selectively improved glucose-stimulated insulin release and glucose tolerance in both normal and diabetic rats. A series of 4-cyclo
