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Manganese(I)-Catalyzed Enantioselective C(sp)-C(sp) Bond-Forming for the Synthesis of Skipped Dienes with Synergistic Aminocatalysis.
Angew Chem Int Ed Engl
May 2024
State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, China.
Mn(I)-catalyzed enantioselective C-C bond-forming reactions represent a great challenge in homogeneous catalysis primarily due to a limited understanding of its mechanistic principles. Herein, we have developed an interesting catalytic strategy that leverages a synergistic combination of a dimeric manganese(I) catalyst and a chiral aminocatalyst to address this issue. A range of conjugated dienals and trienals can exclusively proceed 1,4-hydroalkenylation by using readily available aromatic and aliphatic alkenyl boronic acids as coupling partners, producing a rich library of skipped diene aldehydes in synthetically useful yields and high levels of enantioselectivities.
View Article and Find Full Text PDFComputational Study of the Stability of Pyrrolidine-Derived Iminium Ions: Exchange Equilibria between Iminium Ions and Carbonyl Compounds.
ACS Omega
June 2022
Organic Chemistry Section, Facultat de Química, Universitat de Barcelona, Diagonal 645, 08028 Barcelona, Catalonia, Spain.
The tendency of carbonyl compounds to form iminium ions by reaction with pyrrolidine or chiral pyrrolidine derivatives (in other words, the relative stability to hydrolysis of these iminium ions) has been computationally examined, mainly using the M06-2X/6-311+G(d,p) method. We have thus obtained the equilibrium positions for R-CH=O + CH=CH-CH=NR* → R-CH=NR* + CH=CH-CH=O reactions and for related exchanges. In these exchanges, there is a transfer of a secondary amine between two carbonyl compounds.
View Article and Find Full Text PDFPolyunsaturated lipids and vitamin A oxidation during cod liver oil in vitro gastrointestinal digestion. Antioxidant effect of added BHT.
Food Chem
October 2017
Food Technology, Faculty of Pharmacy, Lascaray Research Center, University of the Basque Country (UPV/EHU), Paseo de la Universidad n° 7, 01006 Vitoria-Gasteiz, Spain. Electronic address:
The extent of cod liver oil hydrolysis and oxidation during in vitro gastrointestinal digestion was investigated by Proton Nuclear Magnetic Resonance (H NMR) and Solid Phase Microextraction-Gas Chromatography/Mass Spectrometry (SPME-GC/MS). These techniques evidenced the degradation of polyunsaturated ω-3 and ω-6 lipids and, for the first time, that of vitamin A, naturally present in cod liver oil. Cis,trans-conjugated dienes associated with hydroperoxides, as well as monoepoxides, cis,trans-2,4-alkadienals, 4-hydroperoxy- and 4-hydroxy-2-alkenals, and several vitamin A derived metabolites were generated.
View Article and Find Full Text PDFControlling Asymmetric Remote and Cascade 1,3-Dipolar Cycloaddition Reactions by Organocatalysis.
J Am Chem Soc
May 2016
Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark.
The regio- and stereoselective control of cycloaddition reactions to polyconjugated systems has been demonstrated by applying asymmetric organocatalysis. Reaction of 2,4-dienals with nitrones allows for a highly regio- and stereoselective 1,3-dipolar cycloaddition in the presence of an aminocatalyst. The first cycloaddition on the remote olefin can be followed either by a cascade reaction or by other selective reactions of the remaining olefin.
View Article and Find Full Text PDFTotal synthesis of dermostatin A.
J Org Chem
October 2011
Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, United States.
The concise total synthesis of dermostatin A is described. Highlights include a two-directional application of the asymmetric acetate aldol method developed in our lab, a novel diastereotopic-group-selective acetal isomerization for terminus differentiation, and a selective cross-metathesis reaction between a terminal olefin and a trienal. A study of the scope and viability of similar cross-metathesis reactions is also described.
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