Regioselective TEMPO oxidation of 2-alkylidene-1,3-propanediols to (E)-2-hydroxymethyl-2-alkenals and application to 4-alkylidene-2-penten-5-olide synthesis |
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| Authors: | Wei Peng |
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| Affiliation: | Department of Medicinal and Bioengineering Science, Graduate School of Natural Science and Technology, Okayama University, Tsushima-naka, Kita-ku, Okayama 700-8530, Japan |
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| Abstract: | The oxidation system comprised of TEMPO and (diacetoxyiodo)benzene (stoichiometric) is enhanced during the conversion of primary alcohols to aldehydes by adding a catalytic amount of acids, p-TsOH and PPTS. 2-Alkylidene-1,3-propanediols, available from 1,3-dihydroxyacetone, are oxidized under the stated conditions to the corresponding (E)-2-hydroxymethyl-2-alkenals, which are utilized as an intermediate for the expeditious synthesis of 4-alkylidene-2-penten-5-olides. |
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| Keywords: | Oxidation TEMPO (Diacetoxyiodo)benzene 2-Alkenal 2-Penten-5-olide |
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