Reaction of C3 and C4 ketoses with alkenals and alkenones in water |
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Authors: | Hiroyuki Saimoto Tomoyuki Onitsuka Satoko Okabe Minoru Morimoto |
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Affiliation: | a Department of Materials Science, Faculty of Engineering, Tottori University, Koyama 680-8552, Tottori, Japan b Division of Instrumental Analysis, Research Center for Bioscience and Technology, Tottori University, Koyama 680-8550, Tottori, Japan |
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Abstract: | Treatment of 1,3-dihydroxyacetone and acrolein with aqueous KOH gave a tetrahydrofuran derivative, 1,4-dihydroxy-3,7-dioxabicyclo3.3.0]octane, in 80% yield. Similarly, 6-alkyl substituted 1,4-dihydroxy-3,7-dioxabicyclo3.3.0]octanes were obtained by reaction of 1,3-dihydroxyacetone with various α,β-unsaturated aldehydes. In the cases of long chain alkenals, the reaction was effectively accelerated in the presence of organic co-solvent. On the other hand, the corresponding tricyclic products were synthesized by reaction of 1,3-dihydroxyacetone with cyclic enones, such as 2-cyclopentenone and 2-cyclohexenone. This method was successfully applied to the reaction of a tetrulose in the absence of any protecting groups. |
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Keywords: | Dihydroxyacetone Erythrulose Water One-pot reaction Tetrahydrofurans |
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