764-60-3Relevant articles and documents
Synthesis of α,β-unsaturated epoxy ketones utilizing a bifunctional sulfonium/phosphonium ylide
Eskandari, Roozbeh,Hess, Jeremy P.,Tochtrop, Gregory P.
supporting information, p. 7136 - 7139 (2021/07/28)
Herein, a new protocol for rapid synthesis of α,β-unsaturated epoxy ketones utilizing a bifunctional sulfonium/phosphonium ylide is described. This approach comprises two sequential chemoselective reactions between sulfonium and phosphonium ylides and two distinct aldehydes, which allows for the rapid construction of a variety of unsymmetric α,β-unsaturated epoxy ketones. This methodology allows the rapid construction of the core reactive functionality of a family of lipid peroxidation products, the epoxyketooctadecenoic acids, but can be further broadly utilized as a useful synthon for the synthesis of natural products, particularly those derived from oxidized fatty acids. Accordingly, a protocol utilizing this approach to synthesize the epoxyketooctadecenoic acid family of molecules is described.
Enantioselective Rhodium-Catalyzed Dimerization of ω-Allenyl Carboxylic Acids: Straightforward Synthesis of C2-Symmetric Macrodiolides
Steib, Philip,Breit, Bernhard
supporting information, p. 6572 - 6576 (2018/05/08)
Herein, we report on the first enantioselective and atom-efficient catalytic one-step dimerization method to selectively transform ω-allenyl carboxylic acids into C2-symmetric 14- to 28-membered bismacrolactones (macrodiolides). This convenient asymmetric access serves as an attractive route towards multiple naturally occuring homodimeric macrocyclic scaffolds and demonstrates excellent efficiency to construct the complex, symmetric core structures. By utilizing a rhodium catalyst with a modified chiral cyclopentylidene-diop ligand, the desired diolides were obtained in good to high yields, high diastereoselectivity, and excellent enantioselectivity.
Synthesis and the crystal structure of dimeric 1-hydroxyhexane-2,3-dione and the spectral characteristics of a model acireductone
Trzewik, Bartosz,Chruszcz-Lipska, Katarzyna,Mi?aczewska, Anna,Opalińska-Piskorz, Joanna,Karcz, Robert,Grybo?, Robert,Oszajca, Marcin,Luberda-Durna?, Katarzyna,?asocha, Wies?aw,Fitch, Andy,Sulikowski, Bogdan,Borowski, Tomasz
supporting information, p. 9291 - 9303 (2016/11/11)
An efficient synthetic route to 1-hydroxyhexane-2,3-dione, which is a tautomeric form of a model acireductone, is presented here. Interestingly, the compound was found to crystallise as a stable dimer, a molecule of which contains a 1,3-dioxolane ring. The dimer structure was solved using the PXRD (powder X-ray diffraction) method and confirmed by NMR, IR, and Raman spectroscopy and DFT calculations. The title compound dissolves in water with the formation of several monomeric forms of the model acireductone as revealed by UV-Vis and NMR spectra. The extinction coefficients of the neutral and anionic forms of the monomer were also determined.