Selective Mono-reduction of Pyrrole-2,5 and 2,4-Dicarboxylates

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  • Yasui Eiko
    Department of Applied Chemistry, Kogakuin University Department of Chemistry and Life Science, Kogakuin University
  • Tsuda Jyunpei
    Department of Applied Chemistry, Kogakuin University
  • Ohnuki Satoshi
    Department of Applied Chemistry, Kogakuin University
  • Nagumo Shinji
    Department of Applied Chemistry, Kogakuin University Department of Chemistry and Life Science, Kogakuin University

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<p>Pyrrole-2,5-dicarboxylates were rapidly and selectively reduced to the corresponding mono-alcohol using 3 eq of diisobutylaluminum hydride at 0°C. Pyrrole-2,4-dicarboxylate showed the same reactivity; however, the selectivity decreased with pyrrole-3,4-dicarboxylate. When the nitrogen atom of the pyrrole-2,5-dicarboxylate is protected with a benzyl group, selective mono-reduction does not occur. Considering that furan-2,5-dicarboxylates did not give the corresponding mono-alcohol under the same conditions, the unprotected nitrogen atom of pyrrole apparently plays an important role in this selective mono-reduction.</p>

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