192433-20-8Relevant academic research and scientific papers
A versatile approach to functionalized cyclic ketones bearing quaternary carbon stereocenters via organocatalytic asymmetric conjugate addition of nitroalkanes to cyclic β-substituted α,β-Enones
Yu, Si-Jia,Zhu, Ya-Nan,Ye, Jian-Liang,Huang, Pei-Qiang
, (2021)
A versatile organocatalytic asymmetric conjugate addition of nitroalkanes to β-substituted cyclic α,β-enones to yield cyclic ketones bearing all-carbon quaternary stereogenic centers at β-C has been developed. This is an extension of the method that we de
Formaldehyde dialkylhydrazones as neutral formyl anion and cyanide equivalents: Nucleophilic addition to conjugated enones
Diez,Fernandez,Gasch,Lassaletta,Llera,Martin-Zamora,Vazquez
, p. 5144 - 5155 (2007/10/03)
A versatile methodology for the nucleophihc formylation and cyanation of conjugated enones is reported. The procedure is based on the use of formaldehyde dimethylhydrazone, which, acting as a neutral formyl anion equivalent, adds to preformed trialkylsilyl-enone complexes. Both 4-(silyl- oxy)-3-enal hydrazones 3 or deprotected 4-oxo aldehyde monohydrazones 4 can be obtained at products depending on quenching conditions. In full analogy, an asymmetric version of the reaction using chiral formaldehyde SAMP- hydrazone as a neutral synthon of the chiral formyl anion has been developed, giving rise to the corresponding adducts 5 and 6 in good yields and with excellent diastereoselectivities (de 85-≤98%). Ozonolysis or HCl-mediated hydrolysis of adducts 4 and 6 readily affords racemic and optically enriched 4-oxo aldehydes 7, respectively. Additionally, high-yielding MMPP-oxidative cleavage of 4-oxo hydrazones 4 and 6 has been performed to obtain 4-oxo nitriles 8 in racemic and optically enriched forms, respectively. In this way, interesting chiral bifunctional building blocks, some of them bearing newly created stereogenic quaternary centers, have been efficiently synthesized.
Regioselectivity in the Intramolecular Carbon-Hydrogen Insertion in Metal-catalysed Decomposition of some cis-1-Methyl-3-arylcyclohexyl Diazomethyl Ketones. A Highly Efficient Homogeneous Nickel Catalyst for Carbenoid Insertion
Chakraborti, Asit K.,Ray, Jayanta K.,Kundu, Kalyan K.,Chakrabarty, Sephali,Mukherjee, Debabrata,Ghatak, Usha Ranjan
, p. 261 - 273 (2007/10/02)
The comparative effectiveness of a variety of copper catalysts and a few transition-metal chelates have been examined in the carbenoid decomposition of cis,cis-1,5-dimethyl-3-phenylcyclohexyl diazomethyl ketone (11),
