Acid catalyzed aldol condensations of ketones with glyoxylic acid: A simple single-step synthesis of 4-oxo-2,5-heptdienedioic acids

References

• Mahrwald, R. Aldol Reactions; Springer Science & Business Media: Heidelberg, 2009.
   Google Scholar
• Olsen, S.; Balk, H.; Finholdt, K. Über Die Säurekatalysierte Aldolreaktion Des Formaldehyds Mit Lävulinsäure, III. Zur Kenntnis Des 3.5.5-Tris Hydroxymethyl-Dihydro-Desoxy-Patulinsäurelactons. Justus Liebigs Ann. Chem. 1960, 635, 52–66. DOI:10.1002/jlac.19606350106
   Google Scholar
• Olsen, S.; Henriksen, A.; Brauer, R. Über Aldolreaktionen Des Formaldehyds Und Ihre Umkehrbarkeit Vergleichende Studien Zum Mechanismus Der Tollens-Reaktion, Der Mannich-Reaktion Und Der Säurekatalysierten Aldolreaktion Des Formaldehyds. Justus Liebigs Ann. Chem. 1959, 628, 1–36. DOI:10.1002/jlac.19596280102
   Google Scholar
• Olsen, S.; Clauson-Kaas, N.; Clauson-Kaas, N.; Virtanen, A. I. Über Die Umsetzung Von Formaldehyd Mit Ketocarbonsäuren II. Lävulinsäure. Synthese Des 3,5,5-Trimethylol-Dihydro-Deoxy-Patulinsäure-Lactons. Acta Chem. Scand. 1955, 9, 101–110. DOI:10.3891/acta.chem.scand.09-0101
   Google Scholar
• Amarasekara, A. S.; Wiredu, B. Single Reactor Conversion of Corn Stover Biomass to C5–C20 Furanic Biocrude Oil Using Sulfonic Acid Functionalized Brönsted Acidic Ionic Liquid Catalysts. Biomass Conv. Bioref. 2014, 4, 149–155. DOI:10.1007/s13399-013-0098-y
   Google Scholar
• Amarasekara, A. S.; Hawkins, S. A. Synthesis of Levulinic Acid–Glycerol Ketal–Ester Oligomers and Structural Characterization Using NMR Spectroscopy. Europ. Polym. J. 2011, 47, 2451–2457. DOI:10.1016/j.eurpolymj.2011.09.007
   Web of Science ®Google Scholar
• Amarasekara, A. S.; Singh, T. B.; Larkin, E.; Hasan, M. A.; Fan, H.-J. NaOH Catalyzed Condensation Reactions between Levulinic Acid and Biomass Derived Furan-Aldehydes in Water. Ind. Crop.Product 2015, 65, 546–549. DOI:10.1016/j.indcrop.2014.10.005
   Web of Science ®Google Scholar
• Amarasekara, A. S.; Ha, U.; Fonari, M. S.; Bejagam, S. N.; Margetić, D. Sulfuric Acid and Amberlyst-H + Catalyzed Condensation Reactions of Renewable Keto Acids with Paraformaldehyde: synthesis of a New Dispiro Bis-Lactone Ring System 2,9,13-Trioxadispiro[4.1.4.3]Tetradecane-3,6,10-Trione. RSC Adv. 2017, 7, 23917–23923. DOI:10.1039/C7RA02303K
   Web of Science ®Google Scholar
• Amarasekara, A. S.; Ha, U. Acid Catalyzed Condensation of Levulinic Acid with Glyoxylic Acid: synthesis of 1-Methyl-2,8-Dioxabicyclo[3.3.0]Oct-4-Ene-3,7-Dione. Tet. Lett. 2016, 57, 2598–2600.
   Web of Science ®Google Scholar
• Sun, Z. C.; Eli, W.; Xu, T. Y.; Zhang, Y. G. Oxidation of Glyoxal with Hydroperoxide Compounds Prepared from Maleic Acid by Ozonation to Produce Glyoxylic Acid. Ind. Eng. Chem. Res. 2006, 45, 1849–1852.
   Web of Science ®Google Scholar
• Isobe, K.; Nishise, H. A Method for Glyoxylic Acid Production Using Cells of Alcaligenes Sp. GOX373. J. Biotechnol. 1999, 75, 265–271.
   Web of Science ®Google Scholar
• Boughton, B. A.; Griffin, M. D. W.; O'Donnell, P. A.; Dobson, R. C. J.; Perugini, M. A.; Gerrard, J. A.; Hutton, C. A. Irreversible Inhibition of Dihydrodipicolinate Synthase by 4-Oxo-Heptenedioic Acid Analogues. Bioorg. Med. Chem. 2008, 16, 9975–9983.
   PubMed Web of Science ®Google Scholar
• Hiroshi, M. Bull. Chem. Soc. Japan 1953, 26, 302–304.
   Google Scholar
• Jakubcová, M.; Végh, D.; Kožíšek, J.; Dvorský, A. A Convenient Synthesis of Halogenated Spiro Bi-2(5H)-Furanones. Synth. Commun. 1994, 24, 1333–1338.
   Web of Science ®Google Scholar
• Amarasekara, A. S. Acidic Ionic Liquids. Chem. Rev. 2016, 116, 6133–6183.
   PubMed Web of Science ®Google Scholar
• Wiredu, B.; Amarasekara, A. S. Catal. Commun. 2014, 48, 41–44.
   Web of Science ®Google Scholar
• Nguyen, T. B.; Al-Mourabit, A. Remarkably High Homoselectivity in [2 + 2] Photodimerization of Trans-Cinnamic Acids in Multicomponent Systems. Photochem. Photobiol. Sci. 2016, 15, 1115–1119.
   PubMed Web of Science ®Google Scholar
• Bertmer, M.; Nieuwendaal, R. C.; Barnes, A. B.; Hayes, S. E. J. Phys. Chem. B. [Database] 2006, 110, 6270–6273.
   PubMed Web of Science ®Google Scholar
• Benedict, J. B.; Coppens, P. Kinetics of the Single-Crystal to Single-Crystal Two-Photon Photodimerization of Alpha-Trans-Cinnamic Acid to Alpha-Truxillic Acid. J. Phys. Chem. A. 2009, 113, 3116–3120.
   PubMed Web of Science ®Google Scholar
• Ghosn, M. W.; Wolf, C. Stereocontrolled Photodimerization with Congested 1,8-Bis(4'-Anilino)Naphthalene Templates. J. Org. Chem. 2010, 75, 6653–6659.
   PubMed Web of Science ®Google Scholar
• Corse, J.; Finkle, B. J.; Lundin, R. E. Confirmation of the Tricyclo[6,2,0,03,6]-Decane Structure for the Photodimer of Dimethyl 3-Oxo-1,4-Pentadiene-1,5-Dicarboxylate. Tet. Lett. 1961, 2, 1–4.
   Google Scholar
• Green, B. S.; Schmidt, G. Topochemically-Controlled Solid-State Photodimerization to a Tricyclo[6.2.0.0.3,6]-Decane Derivative. Tet. Lett. 1970, 11, 4249–4252.
   Google Scholar