15732-85-1Relevant academic research and scientific papers
Enantioconvergent alkylation of ketones with racemic secondary alcohols: Via hydrogen borrowing catalysis
Cheang, Daniella M. J.,Armstrong, Roly J.,Akhtar, Wasim M.,Donohoe, Timothy J.
supporting information, p. 3543 - 3546 (2020/04/03)
An enantioconvergent method for the alkylation of o-disubstituted aryl ketones with racemic secondary alcohols is described. This process is mediated by a commercially available iridium catalyst and proceeds via hydrogen borrowing catalysis. The highly enantioenriched β-substituted ketone products were readily cleaved to a wide range of functional groups via retro-Friedel-Crafts acylation.
Cu-Catalyzed Hydroxymethylation of Unactivated Alkyl Iodides with CO To Provide One-Carbon-Extended Alcohols
Zhao, Siling,Mankad, Neal P.
supporting information, p. 5867 - 5870 (2018/04/17)
We have developed a reductive carbonylation method by which unactivated alkyl iodides can be hydroxymethylated to provide one-carbon-extended alcohol products under Cu-catalyzed conditions. The method is tolerant of alkyl β-hydrogen atoms, is robust towards a wide variety of functional groups, and was applied to primary, secondary, and tertiary alkyl iodide substrates. Mechanistic experiments indicate that the transformation proceeds by atom-transfer carbonylation (ATC) of the alkyl iodide followed in tandem by two CuH-mediated reductions in rapid succession. This radical mechanism renders the Cu-catalyzed system complementary to precious-metal-catalyzed reductive carbonylation reactions.
Disubstituted beta-lactones as inhibitors of N-acylethanolamine acid amidase (NAAA)
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Page/Page column 96, (2016/06/28)
The present invention provides compounds and pharmaceutical compositions for inhibiting N-acylethanolamine acid amidase (NAAA). Inhibition of NAAA is contemplated as a method to sustain the levels of palmitoylethanolamide (PEA) and oleylethanolamide (OEA), two substrates of NAAA, in conditions characterized by reduced concentrations of PEA and OEA. The invention also provides methods for treating inflammatory diseases and pain, and other disorders in which decreased levels of PEA and OEA are associated with the disorder.
Ring-opening of cyclic ethers with carbon-carbon bond formation by Grignard reagents
Christensen, Stig Holden,Holm, Torkil,Madsen, Robert
, p. 4942 - 4946 (2014/07/07)
The ring-opening of cyclic ethers with concomitant C-C bond formation was studied with a number of Grignard reagents. The transformation was performed in a sealed vial by heating to ~160 °C in an aluminum block or at 180 °C in a microwave oven. Good yields of the product alcohols were obtained with allyl- and benzylmagnesium halides when the ether was tetrahydrofuran or 3,3-dimethyloxetane. Lower yields were obtained with substituted tetrahydrofurans while no ring-opening was observed with tetrahydropyran. Only highly reactive allyl and benzyl Grignard reagents participated in the transformation while no reaction occurred with other alkylmagnesium halides.
Synthesis, biological evaluation, and 3D QSAR study of 2-methyl-4-oxo-3-oxetanylcarbamic acid esters as N -acylethanolamine acid amidase (NAAA) inhibitors
Ponzano, Stefano,Berteotti, Anna,Petracca, Rita,Vitale, Romina,Mengatto, Luisa,Bandiera, Tiziano,Cavalli, Andrea,Piomelli, Daniele,Bertozzi, Fabio,Bottegoni, Giovanni
supporting information, p. 10101 - 10111 (2015/02/02)
N-(2-Oxo-3-oxetanyl)carbamic acid esters have recently been reported to be noncompetitive inhibitors of the N-acylethanolamine acid amidase (NAAA) potentially useful for the treatment of pain and inflammation. In the present study, we further explored the
DISUBSTITUTED BETA-LACTONES AS INHIBITORS OF N-ACYLETHANOLAMINE ACID AMIDASE (NAAA)
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Paragraph 0271, (2013/06/06)
The present invention provides compounds and pharmaceutical compositions for inhibiting N-acylethanolamine acid amidase (NAAA). Inhibition of NAAA is contemplated as a method to sustain the levels of palmitoylethanolamide (PEA) and oleylethanolamide (OEA), two substrates of NAAA, in conditions characterized by reduced concentrations of PEA and OEA. The invention also provides methods for treating inflammatory diseases and pain, and other disorders in which decreased levels of PEA and OEA are associated with the disorder.
Nickel(0)/NaHMDS adduct-mediated intramolecular alkylation of unactivated arenes via a homolytic aromatic substitution mechanism
Beaulieu, Louis-Philippe B.,Roman, Daniela Sustac,Vallee, Frederic,Charette, Andre B.
supporting information; experimental part, p. 8249 - 8251 (2012/09/07)
A variety of polycycles can be synthesized via an intramolecular alkylation cyclization promoted by Ni(PPh3)4 and NaHMDS. Mechanistic investigations support the catalytic nature of Ni0 in the course of TEMPO scavenging experiments and its association with the substrate and NaHMDS to form an adduct by DOSY NMR.
